politoxicomania (Stranger)
09-09-03 13:39
No 457963
       Succinaldehyd  Bookmark   

someone out there who prepared succinaldeyd before ?
i figuered out 2,5-dimethoxytetrahydrofuran as a precursor
but it is very expansive,
could someone give a ref about a syntheses from
2,4-butandiacid  or butandiacidanhydrid ?
must be possible!
thanks
smile 		 
 
 
 
    Vitus_Verdegast
(Hive Bee)
09-09-03 15:36
No 457988
       2,5-dimethoxytetrahydrofuran  Bookmark   

It is not THAT expensive, Fisher has it for $30/100 g and I've seen one photographical supplier that sold it for $3.95/10 g.

Please provide a link or a reference to the procedure you mean.
A Dream Within A Dream (http://www.poedecoder.com/Qrisse/works/dreamw.html) 		 
 
 
 
    politoxicomania
09-09-03 16:17
       Price
(Rated as: no sources!) 		 Bookmark   
 
 
 
    politoxicomania
(Stranger)
09-09-03 16:52
No 458006
       no sources  Bookmark   

sorry sorry sorry
i sould read the manual before posting 		 
 
 
 
    roger2003
(Hive Bee)
09-11-03 04:55
No 458404
       succindialdehyde  Bookmark   

2,5 Diemthoxytetrahydrofuran can be converted in quantitative yield to succindialdehyde with HCL or H2SO4 in aqueous solutions without workup.

There is also a way from 1,4 - butanediol to succindialdehyde. If i remember right, there is a patent, maybe 1975, to BASF

Ullmann`s:

Succinaldehyde (1,4-Butanedial)

Some physical properties of succinaldehyde and its CAS registry number are given in Table (8). To avoid spontaneous polymerization of anhydrous succinaldehyde, it is best stored as a cyclic acetal, e.g., 2,5 dimethoxytetrahydrofuran. Aqueous solutions consist mainly of the cyclic hemiacetal 2,5-dihydroxytetrahydrofuran.
Production. Succinaldehyde is prepared by various routes, e.g., reaction of chlorine with tetrahydrofuran and subsequent acid hydrolysis. Hydroformylation of acrolein acetals (mostly cyclic) yields a mixture of 2- and 3-(1,3-dioxan-2-yl)propanal. Hydrolysis of the latter forms 1,4-butanedial Post 141 (not existing).
 
Due to the similar chemical properties, succinaldehyde has been replaced extensively by glutardialdehyde, diminishing its commercial importance significantly.
Uses. Succinaldehyde is used as disinfectant, biological fixative, and cross-linker in thermosetting resins.


Post 141 (not existing)  M. Tamura, S. Kumano, Chem. Econ. Eng. Rev. 12  (1980) 32.J. Maeda, R. Yoshida, Bull Chem. Soc. Jpn. 41 (1968) 2969.BASF, DE 2 401 553, 1975(R. Kummer).
roger2003 		 
 
 
 
    Rhodium
(Chief Bee)
09-11-03 06:25
No 458411
       synthesis of succindialdehyde  Bookmark   

I researched the synthesis of succindialdehyde a few years ago, and I found that there is really no better method (in terms of ease, time and money) than the acid hydrolysis of commercially available 2,5-dimethoxytetrahydrofuran, even if it isn't the cheapest of chemicals. The second best method is the ring-opening of pyrrole with hydroxylamine, followed by hydrolysis of the formed  succindialdehyde dioxime. Refs upon request. 		 
 
 
 
    roger2003
(Hive Bee)
09-12-03 06:51
No 458658
       succindialdehyde  Bookmark   

There are also a lot of ways from furan to 2,5 - dimethoxytetrahydrofuran

Organic Syntheses CV 5, 403 		 
 
 
 
    Rhodium
(Chief Bee)
09-12-03 11:23
No 458701
       2,5-Dimethoxy-tetrahydrofuran from Furan
(Rated as: good read) 		 Bookmark   

Organic Syntheses, CV 5, 403 (http://www.orgsyn.org/orgsyn/prep.asp?prep=cv5p0403) is unfortunately a synthesis of  2,5-dimethoxy-2,5-dihydrofuran from furan - to arrive at 2,5-dimethoxy-tetrahydrofuran you need to subject the dihydrofuran to catalytic hydrogenation (best accomplished with Raney-Ni/80–100°C/1700–2000 psi./45–60 min.), see the following ref:

Preparation and Reactions of Dialkoxytetrahydrofurans
Jørgen Fakstorp, Dolores Raleigh, L. E. Schniepp
J. Am. Chem. Soc. 72(2), 869-874 (1950) 		 
 
 
 
    politoxicomania
(Stranger)
09-12-03 12:39
No 458720
       too expensive  Bookmark   

good post
good refs
but too expensive
better keep it simple, slow and cheap 		 
 
 
 
    pHarmacist
(pHantasticant)
09-12-03 21:18
No 458796
       i see...  Bookmark   

better keep it simple, slow and cheap

...and that would bee?
Point... Counter Point...