Hydrochloric Acid → 1,1,1-Trichloro-4-methylpent-4-en-2-ol

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Reaction Steps

To the optically-active catalyst of Example 1 (a) (total product) under nitrogen was added a solution of chloral (3.3 ml, 33.8 mmole) in dichloromethane (dried over calcium hydride) (30 ml). After cooling the solution to 0°-5° C., isobutene gas (2.84 g, 50 mmole) was bubbled through the mixture over about 1 min. At this stage the temperature of the mixture was not allowed to rise above 20° C. After stirring the mixture at 10°-15° C. for up to 20 h, it was poured into 10% hydrochloric acid (30 ml). After shaking the phases, the aqueous layer was separated and extracted with fresh dichloromethane (2×30 ml). The combined organic extracts were washed with water (30 ml) and dried (MgSO4). Concentration of the extract gave a red oil (6.55 g, 95%) which was distilled to give the product as a colourless oil, with physical characteristics identical to those reported in the literature.

Provenance & Evidence