Hydrogen Bromide → 1-Hydroxymethyl-2-(1'-bromoethyl)-benzene

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Reaction Steps

Similarly prepared from phthalic anhydride and methylmalonic acid were 2-(1'-oxopropyl)benzoic acid and thence 1-hydroxymethyl-2-(1'-hydroxypropyl)benzene (both as oils). (b) (i) 1-Hydroxymethyl-2-(1'-hydroxyethyl)benzene (10 g) was dissolved in dichloromethane (200 ml) and was saturated with hydrogen bromide gas. The solution was stirred for 2 hr. and volatile materials were evaporated to give 1-hydroxymethyl-2-(1'-bromoethyl)-benzene as an oil. Thionyl chloride (30 ml) was added to the oil and the solution was stirred for 1 hr; evaporation of thionyl chloride gave 1-chloromethyl-2-(1'-bromoethyl)benzene which was used immediately. (ii) Similarly prepared from 1-hydroxymethyl-2-(1'-hydroxypropyl)benzene were 1-hydroxymethyl-2-(1'-bromopropyl)benzene and thence 1-chloromethyl-2-(1'-bromopropyl)benzene (both as oils).

Provenance & Evidence