Water → 4,4-dimethyl-2-(4-methylphenyl)-5H-1,3-oxazole

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Reaction Steps

2-Amino-2-methyl-propanol (14.5 ml, 151 mmol) was stirred in 30 ml CH2Cl2 at 0° C. 4-Methylbenzoyl chloride (p-toluoyl chloride) (4c) (11.69 g, 75.6 mmol) was added dropwise. 4-Methylbenzoyl chloride may be prepared by conventional processes. The mixture was stirred for 4 hrs, at which time 11 ml of SOCl2 (151 mmol) was added slowly. The mixture was warmed to room temperature overnight. Water (30 ml) was added, the layers separated, and the organic layer washed with water (5×20 ml). The combined water layer was rinsed once with 15 ml CH2Cl2, and then basified with aqueous ammonia. The cloudy mixture was extracted with CH2Cl2 (3×30 ml), dried over MgSO4, filtered and the solvent evaporated to yield 10.7 g as a white crystalline solid (75% yield).

Provenance & Evidence