Ethanol → HCID 54317528, compound

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (3 ml) was added dropwise over a period of 2 minutes to ethanol (50 ml) at -10° C. whilst under an atmosphere of argon. The reaction mixture was stirred at -10° C. for 20 minutes and then allowed to warm to ambient temperature. A solution of 3-ethyl-4-hydroxybenzoic acid (3.5 g) in ethanol was added to the reaction mixture dropwise, with cooling (ice-bath). The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The ethanol was removed by evaporation and the residue was partitioned between ethyl acetate (100 ml) and 1M aqueous sodium hydroxide solution (50 ml). The phases were separated and the aqueous phase washed with ethyl acetate (50 ml). The ethyl acetate extracts were combined, washed with water (50 ml) brine (50 ml), dried (MgSO4) and evaporated. The residue, an oil, crystallised on standing to give a solid which was triturated with 10% diethyl ether/pentane to give ethyl 3-ethyl-4-hydroxybenzoate as a solid (1.4 g), m.p. 73°-74° C.; microanalysis, found: C, 68.4; H, 7.7%; C11H14O3 requires: C, 68.0; H, 7.3%; NMR: 1.15(3H,t), 1.3(3H,t), 2.55(2H,q), 4.25(2H,q), 6.85(2H,d), 7.65(2H,m), 10.15(1H,s).

Provenance & Evidence