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To a mixture containing 2.57 g, 15 mmol, of phenyltrimethylammonium chloride, 1, and 1.95 g, 6 mmol, of Cs₂CO₃ in 20 ml of toluene were added 10 mmol of the hydroxy compound. The resulting mixture was heated at reflux for the time indicated in tables 1 and 2. The reaction mixture was then washed first with a 1 M HCl solution, then water, and dried over anhydrous magnesium sulfate. Following evaporation of the solvent under reduced pressure, the crude product was subjected to recrystallization or bulb-to-bulb distillation. The spectroscopic and chromatographic properties of the products were in all cases in full agreement with those of authentic samples.

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Table 1. Alkylation of phenols and alcohols with 1

Entry	Substrate	t/h	Product	Half-lifea	%Yield (isolated)b
1	4-Methoxyphenol	28	1,4-Dimethoxybenzene	30 min	97 (50)
2	3-tert-Butylphenol	27	3-tert-Butylanisole	6 h	99 (92)
3	3-Chlorophenol	6	3-Chloroanisole	10 min	98 (85)
4	4-Bromophenol	11	4-Bromoanisole	3 h	97 (56)
5	4-Fluorophenol	24	4-Fluoroanisole	2 h	95 (60)
6	4-Nitrophenol	48	4-Nitroanisole	23 h	87 (88)
7	1-Naphtol	21	1-Methoxynaphtalene	2.5 h	98 (87)
8	2-Naphtol	2	2-Methoxynaphtalene	10 min	99 (89)
9	1-Phenylethanol	42	1-Methoxy-1-phenylethane	46
10	Cinnamyl alcohol	148	Cinnamyl methyl ether	24 h	98 (66)
11	4-tert-Butylcyclohexanol, cis + trans	102	Methoxy-4-tert-butyl-cyclohexane, cis + trans	38 h

^a Approximate time for 50% conversion
^b GLC yields


Table 2. Selectivity on alkylation with 1

Entry	Substrate	t/h	Product	%Yielda
1	Salicyl alcohol	30	2-Methoxybenzyl alcohol	78
2	3-(2-Hydroxyphenyl)-2-propenoic acid	27	Methyl 3-(2-hydroxyphenyl)-2-propionate	92
3	1,5-Dihydroxy-1,2,3,4-tetrahydronaphtalene	8	1-Hydroxy-5-methoxy-1,2,3,4-tetrahydronaphtalene	99
4	Mandelic acid	8	Menthyl mandelate	94
5	2-Acetamidophenol	7	2-Methoxyacetanilide	99
6	2-Hydroxybenzoic acid	1	Methyl 2-hydroxybenzoate	87
7	2-Cyclohexyl-2-hydroxacetic acid	29	Methyl 2-cyclohexyl-2-hydroxyacetate	99

^a GLC yields