2-Thiocresol → HCID 66221073, compound

Participants

Reaction Steps

To a solution of o-thiocresol (16.89 g, 136 mmol) in acetone (130 ml) is added potassium carbonate (20.5 g, 148 mmol) and a solution of bromoacetaldehyde dimethylacetal (19.93 g, 123 mmol) in acetone (20 ml) and the reaction mixture is stirred at ambient temperature overnight. The solids are filtered and washed with diethyl ether. The filtrate is concentrated and dissolved into ethyl acetate, washed successively with water, 0.5 N NaOH, and 2N NaOH. The combined aqueous fractions are extracted with dichloromethane. The combined organic fractions are dried over anhydrous MgSO4, filtered and concentrated to afford 1-[(2,2-dimethoxyethyl)thio]-2-methyl-benzene as a brown oil (23.4 g, 90%) that is used without further purification. 1H NMR (CDCl3): δ=7.33 (1H, brd), 7.19-7.08 (3H, m), 4.56 (1H, t), 3.38 (6H, s), 3.10 (2H, d), 2.42 (3H, s).

Provenance & Evidence