Hydrochloric Acid → 3-Cyclohexyl-5-chloro-salicylaldehyde

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Reaction Steps

To 100.4 mmol of 4-chloro-2-cyclohexyl phenol in 40 ml of tetrahydrofuran was added dropwise a 3-molar methylmagnesium bromide solution (36.8 ml; 110.4 mmol) in diethyl ether. After two hours of stirring at room temperature, gas evolution ceased. About 90% of the solvent were removed in vacuo and toluene (250 ml), triethylamine (20 ml), and paraformaldehyde (7.53 g; 251 mmol) were added. The mixture was heated to 88° C. and held at this temperature for two hours. After cooling down to room temperature, the yellow solution was introduced into cold hydrochloric acid (1M, 250 ml). The organic phase was separated and dried over sodium sulphate. After removal of the solvent in vacuo, 5-chloro-3-cyclohexyl salicylaldehyde was recrystallized from ethanol at −20° C. Yield: 59%.

Provenance & Evidence