GC_MS (Hive Bee) 02-05-03 22:29 No 404812 |
o-nitrostyrene reference compilation (Rated as: good read) |
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What follows is a compilation of omega-nitrostyrene syntheses taken from Houben-Weyl. There are 5 threads (forum does not accept post with more than 10000 chars, so I split the references up in the most convenient way): - benzaldehydes with nitromethane (pt 1 + 2) - benzaldehydes with nitroethane - benzaldehydes with nitropropane - benzaldehydes with nitrobutane Reference: Houben-Weyl, Methoden der organischen Chemie. Band X/1, Stickstoffverbindungen I, Teil I, pp 342-357 The "PARTS" agree with different pages from H-W. Hence, many references are mentioned several times. Used abreviations for references:
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GC_MS (Hive Bee) 02-05-03 22:32 No 404813 |
benzaldehydes + nitromethane pt 1 (Rated as: good read) |
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Format: precursor, yield, reference(s)
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GC_MS (Hive Bee) 02-05-03 22:34 No 404815 |
benzaldehydes + nitromethane pt 2 (Rated as: good read) |
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Format: precursor, yield, reference(s) PART 5 4-methoxy-2-ethoxybenzaldehyde, *, [1,2] 3-methoxy-4-ethoxybenzaldehyde, 85, [3-7] 4-methoxy-3-ethoxybenzaldehyde, 64, [3,6,8] 3-methoxy-2-propyloxybenzaldehyde, 27, [9] 3-methoxy-2-isopropyloxybenzaldehyde, 29, [9] 3-methoxy-2-butyloxybenzaldehyde, 20, [9] 3-methoxy-2-pentyloxybenzaldehyde, 57, [9] 3-methoxy-2-(3-methylbutyloxy)-benzaldeh 3-ethoxy-2-isopropyloxybenzaldehyde, 52, [9] 3-ethoxy-2-butyloxybenzaldehyde, 66, [9] 3-ethoxy-2-pentyloxybenzaldehyde, 47, [9] 3,4-dibenzyloxybenzaldehyde, *, [8] 3-nitro-2-hydroxybenzaldehyde, *, [10] 3-nitro-4-methoxybenzaldehyde, 74, [10-12] 3-nitro-4-hydroxybenzaldehyde, *, [12] 2-nitro-3-methoxybenzaldehyde, 85, [13] 2-nitro-4-methoxybenzaldehyde, 70, [13] 2-nitro-5-methoxybenzaldehyde, 80, [13] 2-nitro-5-acetoxybenzaldehyde, quant, [14] [1] MGS Rao, C Srikantia, MS Iyengar, Helv 12, 581 (1929) [2] JR Merchant, AJ Mountwala, J Org Chem 23, 1774 (1958) [3] E Spaeth, A Dobrowsky, B 58, 1274 (1934) [4] T Kondo, K Shinozaki, K Ishi, J Pharm Soc Japan 48, 169 (1928); C (1929) I, 1112 [5] K Sawai, J Pharm Soc Japan 49, 260 (1929); C (1929) I, 2749 [6] A Dornow, G Petsch, Ar 284, 153 (1951) [7] KW Bentley, SF Dyke, J Org Chem 22, 429 (1957) [8] JR Merchant, SR Agrawal, J Indian Chem Soc 40, 472 (1963) [CA 59.9846 (1963)] [9] E Profft, Arzneimittel-Forsch 9, 157 (1959) [10] FGP Remfry, Soc 99, 282 (1911) [11] KH Slotta, G Szyszka, B 68, 184 (1935) [12] JP26960 [CA 62.14569 (1965)] [13] GS Sidhu, PB Sattur, SJ Hasan, J Sci Ind Research (India) 19C, 38 (1960) [CA 55.15381 (1961)] [14] RJS Beer, K Clarke, HG Khorana, A Robertson, Soc (1948) 1605 --- PART 6 6-nitro-2-acetoxybenzaldehyde, quant, [1] 2-nitro-4-methylbenzaldehyde, 65, [2] 4-methoxy-3-rhodanbenzaldehyde, *, [3] 2-iodo-3-methoxybenzaldehyde, 75, [2] 2-hydroxy-3-carboxybenzaldehyde, *, [4] 5-bromo-2,3-dimethoxybenzaldehyde, 90, [5,6] 3,5-dibromo-4-hydroxybenzaldehyde, *, [3] 4,5-dimethoxy-2-methylbenzaldehyde, *, [7] 4,5-dimethoxy-2-ethylbenzaldehyde, *, [7] 2,4-dimethoxy-3-methylbenzaldehyde, *, [7] 2,4-dimethoxy-3-ethylbenzaldehyde, *, [7] 4,6-dimethoxy-2-methylbenzaldehyde, *, [5] 2,4-diethoxy-3-methylbenzaldehyde, *, [7] 4,6-diethoxy-2-methylbenzaldehyde, *, [5] 2-methoxy-3,5-dimethylbenzaldehyde, *, [7] 2-methoxy-4,5-dimethylbenzaldehyde, *, [7] 2,4-dimethoxy-3-benzylbenzaldehyde, *, [7] 2,4-diethoxy-3-benzylbenzaldehyde, *, [7] 4-methoxy-6-ethoxy-2-methylbenzaldehyde, 4-methoxy-2,6-dimethylbenzaldehyde, *, [5] 4-ethoxy-2,6-dimethylbenzaldehyde, *, [5] 6-methoxy-2,4-dimethylbenzaldehyde, *, [5] [1] RJS Beer, K Clarke, HG Khorona, A Robertson, Soc (1948) 1695 [2] GS Sidhu, PB Sattur, SJ Hasan, J Sci Ind Research (India) 19C, 38 (1960) [CA 55.15381 (1961)] [3] JP26960 [CA 62.14569 (1965)] [4] FGP Remfry, Soc 99, 282 (1911) [5] JR Merchant, AJ Mountwala, J Org Chem 23, 1774 (1958) [6] VG Voronin, GD Kulikovskaya, LD Magda, Z Org Chim 1,719 (1965) [CA 63.5546 (1965)] [7] JR Merchant, SR Agrawal, J Indian Chem Soc 40, 472 (1963) [CA 59.9846 (1963)] --- PART 7 6-ethoxy-2,4-dimethylbenzaldehyde, *, [1] 4-hydroxy-3,5-dimethoxybenzaldehyde, 97, [2,3] 2,3,4-trimethoxybenzaldehyde, 73, [4] 2,3,5-trimethoxybenzaldehyde, *, [1] 2,4,5-trimethoxybenzaldehyde, *, [5] 3,4,5-trimethoxybenzaldehyde, 78, [2,4,6,7] 3,4,5-triethoxybenzaldehyde, 55, [4] 3,5-dimethoxy-4-ethoxybenzaldehyde, 65, [3] 5-bromo-2-hydroxy-3-methoxybenzaldehyde, 5-iodo-2-hydroxy-3-methoxybenzaldehyde, 26, [8] 5-bromo-4-hydroxy-3-methoxybenzaldehyde, 2-bromo-3,4-dimethoxybenzaldehyde, 77, [11] 5-bromo-3,4-dimethoxybenzaldehyde, 50, [12] " , 80, [13] (different MP) 5-iodo-2,3-dimethoxybenzaldehyde, *, [8] 5-nitro-3,4-dimethoxybenzaldehyde, *, [7] 5-nitro-2,4-dimethoxybenzaldehyde, *, [14] 4-methoxy-2,3,6-trimethylbenzaldehyde, *, [15] 2,5-dimethoxy-3,4-methylenedioxybenzalde [1] JR Merchant, AJ Mountwala, J Org Chem 23, 1774 (1958) [2] F Mauthner, J pr [2] 92, 194 (1915) [3] F Benington, RD Morin, LC Clarke, Am Soc 76, 5555 (1954) [4] KH Slotta, G Szyszka, J pr [2] 137, 339 (1933) [5] MPJM Jansen, R 50, 291 (1931) [6] E Spaeth, M 40, 129 (1919) [7] KH Slotta, G Szyszka, B 98, 184 (1935) [8] E Profft, M Pannach, Ar 299, 633 (1966) [9] ON Tolkachev, VG Voronin, NA Preobrazhenskii, Z Obsc Chim 28, 3320 (1958) [CA 53.14029 (1959)] [10] SP Makarow, J pr 141, 77 (1934) [11] K Bessho, Chem Pharm Bull (Tokyo) 11, 1491 (1963) [12] M Tomita, H Watanabe, J Pharm Soc Japan 58, 223 (1938) [13] H Kondo e.a, Itsuu Kenkyusho Nempo 9, 1 (1958) [CA 54.1399 (1960)] [14] MGS Rao, C Srikantia, MS Iyengar, Helv 12, 581 (1929) [15] JR Merchant, SR Agrawal, J Indian Chem Soc 40, 472 (1963) [CA 59.9846 (1963)] [16] Mannich, M Falber, Ar 267, 601 (1929); C (1930) I, 77 Abusus non tollit usum |
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GC_MS (Hive Bee) 02-05-03 22:57 No 404816 |
benzaldehydes + nitroethane (Rated as: good read) |
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Format: precursor, yield, reference(s) PART 1 benzaldehyde, 85, [5-10] 4-methylbenzaldehyde, 38, [10] 4-trifluoromethylbenzaldehyde, 55, [11] 2-chlorobenzaldehyde, 66, [10,12] 3-chlorobenzaldehyde, 53, [10] 4-chlorobenzaldehyde, 76, [10] 4-hydroxybenzaldehyde, 35, [9,10,12] 2-methoxybenzaldehyde, 91, [13] 3-methoxybenzaldehyde, 54, [12] 4-methoxybenzaldehyde, 60, [6,7,9,10,12,14] 2-ethoxybenzaldehyde, 73, [12] [5] B Priebs, A 225, 319 (1884); DE Worrall, Org Synth Coll Vol 1, 405 (1932) [6] E Knoevenagel, L Walter, B 37, 4502 (1904) [7] GA Alles, Am Soc 54, 271 (1932) [8] HB Hass, AG Susie, RL Heider, J Org Chem 15, 8 (1950) [9] CB Gairaud, GR Lappin, J Org Chem 18, 1 (1953) [10] M Koremura e.a., Takamine Kenkyusho Nempo 13, 212 (1961) [CA 57.16451 (1962)] [11] GB870541; US3117160 [12] O Schales, HA Graefe, Am Soc 74, 4486 (1952) [13] GB671240 [14] FW Hoover, HB Hass, J Org Chem 12, 501 (1947) --- PART 2 2-nitrobenzaldehyde, 46, [1] " , 62, [1] (different MP) 3-nitrobenzaldehyde, 12, [1] 4-nitrobenzaldehyde, 55, [1,2] 4-aminosulfonbenzaldehyde, *, [3] 4-diethylaminobenzaldehyde, 18, [2] 4-acetaminobenzaldehyde, 30, [2] 2,4-dichlorobenzaldehyde, 73, [2] 3,4-dichlorobenzaldehyde, 52, [2] 4-methoxy-3-chloromethylbenzaldehyde, 78, [1] 2-hydroxy-3-methoxybenzaldehyde, 45, [2,4] 4-hydroxy-3-methoxybenzaldehyde, 72, [1,4-6] 3-methoxy-4-benzoyloxybenzaldehyde, 72, [5] 4-hydroxy-3-ethoxybenzaldehyde, 50, [4] 2,3-dimethoxybenzaldehyde, 79, [2,4] 3,4-dimethoxybenzaldehyde, 35, [4,7] 3,4-methylenedioxybenzaldehyde (piperonal), 80, [1,8] 3-methoxy-2-propyloxybenzaldehyde, 71, [9] [1] M Koremura e.a., Takamine Kenkyusho Nempo 13, 212 (1961) [CA 57.16451 (1962)] [2] O Schales, HA Graefe, Am Soc 74, 4486 (1952) [3] JP17017 [CA 60.13184 (1964)] [4] CB Gairaud, GR Lappin, J Org Chem 18, 1 (1953) [5] R Stewart, RH Clark, Canad J Res 26B, 7 (1948) [6] LV Fennoy, J Org Chem 26, 4696 (1961) [7] GA Alles, Am Soc 54, 271 (1932) [8] E Knoevenagel, L Walter, B 37, 4502 (1904) [9] E Profft, Arzneimittel-Forsch 9, 157 (1959) --- PART 3 3-methoxy-2-isopropoxybenzaldehyde, 67, [1] 3-methoxy-2-butyloxybenzaldehyde, 53, [1] 3-methoxy-2-(2-methylpropyloxy)-benzalde 3-methoxy-2-pentyloxybenzaldehyde, 48, [1] 3-methoxy-2-(3-methylbutyloxy)-benzaldeh 3-methoxy-2-hexyloxybenzaldehyde, 64, [1] 3-methoxy-2-octyloxybenzaldehyde, 63, [1] 2-methoxy-3-ethoxybenzaldehyde, 31, [1] 3-ethoxy-2-propyloxybenzaldehyde, 51, [1] 3-ethoxy-2-isopropyloxybenzaldehyde, 62, [1] 3-ethoxy-2-butyloxybenzaldehyde, 60, [1] 3-ethoxy-2-(2-methylpropyloxy)-benzaldeh 3-ethoxy-2-pentyloxybenzaldehyde, 46, [1] 3-ethoxy-2-(3-methylbutyloxy)-benzaldehy 3-ethoxy-2-octyloxybenzaldehyde, 69, [1] 3-ethoxy-2-dodecyloxybenzaldehyde, 77, [1] 2-nitro-5-acetoxybenzaldehyde, *, [2] 5-bromo-2-hydroxy-3-methoxybenzaldehyde, [1] E Profft, Arzneimittel-Forsch 9, 157 (1959) [2] RJS Beer, K Clark, HG Khorana, A Robertson, Soc (1948), 1605 [3] E Profft, M Pannach, Ar 299, 633 (1966) Abusus non tollit usum |
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GC_MS (Hive Bee) 02-05-03 22:59 No 404817 |
benzaldehydes + nitropropane (Rated as: good read) |
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Format: precursor, yield, reference(s) PART 1 benzaldehyde, 70, [1-3] 2-chlorobenzaldehyde, 68, [3] 3-chlorobenzaldehyde, 36, [3] 4-chlorobenzaldehyde, 7, [3] 3-nitrobenzaldehyde, 62, [3] 4-nitrobenzaldehyde, 10, [3] 4-methylbenzaldehyde, 34, [3] 4-hydroxybenzaldehyde, 22, [3] 4-methoxybenzaldehyde, 90, [1,3] 4-hydroxy-3-methoxybenzaldehyde, 54, [3-5] 3,4-methylenedioxybenzaldehyde (piperonal), 48, [3] 3-methoxy-4-benzoyloxybenzaldehyde, *, [4] 3-methoxy-2-propyloxybenzaldehyde, 50, [6] 3-methoxy-2-isopropyloxybenzaldehyde, 21, [6] 3-methoxy-2-butyloxybenzaldehyde, 36, [6] 3-methoxy-2-(2-methylpropyloxy)-benzalde 3-methoxy-2-pentyloxybenzaldehyde, 26, [6] [1] HB Hass, AG Susie, RL Heider, J Org Chem 15, 8 (1950) [2] PC Ferreira, LA de Pontes, Anais fac farm e odontol univ Sao Paulo 12, 1 (1954) [CA 50.10667 (1956)] [3] M Koremura, J agr chem Soc Japan 36, 552 (1962) [CA 62.3962 (1965)] [4] R Stewart, RH Clark, Canad J Res 26B, 7 (1948) [5] CB Gairaud, GR Lappin, J Org Chem 18, 1 (1953) [6] E Profft, Arzneimittel-Forsch 9, 157 (1959) --- PART 2 3-methoxy-2-(3-methylbutyloxy)-benzaldeh 3-methoxy-2-nonyloxybenzaldehyde, 36, [1] 3-ethoxy-2-isopropyloxybenzaldehyde, 14, [1] 3-ethoxy-2-hexyloxybenzaldehyde, 37, [1] 3-ethoxy-2-nonyloxybenzaldehyde, 31, [1] [...] 3-nitro-4-hydroxybenzaldehyde, 50, [5] 3-nitro-4-methoxybenzaldehyde, 40, [5] 3,5-dichloro-4-hydroxybenzaldehyde, 40, [5] [1] E Profft, Arzneimittel-Forsch 9, 157 (1959) [5] JP26960 [CA 62.14569 (1965)] Abusus non tollit usum |
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GC_MS (Hive Bee) 02-05-03 23:00 No 404818 |
benzaldehydes + nitrobutane (Rated as: good read) |
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Format: precursor, yield, reference(s) PART 1 benzaldehyde, 65-70, [2,6] 4-chlorobenzaldehyde, 86, [6] 3-chlorobenzaldehyde, 52, [6] 2-chlorobenzaldehyde, 77, [6] 4-nitrobenzaldehyde, 47, [6] 3-nitrobenzaldehyde, 31, [6] [2] HB Hass, AG Susie, RL Heider, J Org Chem 15, 8 (1950) [6] M Koremura, J agr chem Soc Japan 36, 552 (1962) [CA 62.3962 (1965)] --- PART 2 2-nitrobenzaldehyde, 47, [1] 4-methylbenzaldehyde, 52, [1] 4-methoxybenzaldehyde, 90, [1,2] 4-hydroxybenzaldehyde, 22, [1] 4-hydroxy-3-methoxybenzaldehyde, 23, [1] 3,4-methylenedioxybenzaldehyde (piperonal), 36, [1] 3-thiocyanobenzaldehyde, 40, [3] 4-thiocyanobenzaldehyde, 39, [3] [1] M Koremura, J agr chem Soc Japan 36, 552 (1962) [CA 62.3962 (1965)] [2] HB Hass, AG Susie, RL Heider, J Org Chem 15, 8 (1950) [3] JP19155 [CA 62.7684 (1965)] Abusus non tollit usum |
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Rhodium (Chief Bee) 02-06-03 02:39 No 404884 |
I didn't know Houben Weyl could be that useful... | Bookmark | ||||||
Great! I'm in the process of converting it to HTML and placing it here: ../rhodium /nitrost The nitromethane section is still missing, and I will add it to the document tomorrow and also put <strong> tags around all the square brackets to make the refs more distinct, as in "Part 2" of the nitrobutane section. |
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GC_MS (Hive Bee) 02-06-03 03:01 No 404889 |
Once you know... | Bookmark | ||||||
Once you know how to deal with the Houben-Weyl, it is one of the most valuable works I'm aware of, chemistry wise. It contains many "general procedures", but what I find most interesting is the fact that it gives a good overview of reaction possibilities. For instance, the reduction of amines. Houben-Weyl doesn't list that many direct amphetamine-related reductions, but it gives a very good overview of what functional groups can be reduced to amines, and what kind of chemicals can be used to achieve that reduction. As such, I have often found it a very good starting point. Abusus non tollit usum |
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Aurelius (Hive Addict) 02-06-03 05:18 No 404931 |
<strong> | Bookmark | ||||||
the 'strong' tags should be used in place of 'b' at the hive? or does it really matter? |
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GC_MS (Hive Bee) 02-06-03 05:56 No 404949 |
strong | Bookmark | ||||||
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Rhodium (Chief Bee) 02-06-03 09:31 No 405006 |
Yup, I'm talking about my own HTML, the Hive... | Bookmark | ||||||
Yup, I'm talking about my own HTML, the Hive markup only supports the [b] tag at the moment. |
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roger2003 (Newbee) 02-06-03 16:22 No 405099 |
The ref. literature (thread 404813) : B ... | Bookmark | ||||||
The ref. literature (in Post 404813 (GC_MS: "benzaldehydes + nitromethane pt 1", Methods Discourse)) : [1] B Priebs, A 225, 319 (1884); DE Worrall, Org Synth Coll Vol I, 405 (1932) must be changed to: Org Synth C V 1, 413 |
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