Hexane → 6-Hydroxyhexanoic Acid

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Reaction Steps

The above solid is suspended in 300 ml of dimethylformamide under a nitrogen atmosphere, cooled to 0° C., treated with 35 g (510 mmol) of imidazole, stirred for 15 min at 0° C. and 15 min at ambient temperature, cooled to 0° C. and treated with 39 g (260 mmol) of t-butyldimethylsilylchloride. The resulting solution is then allowed to warm to ambient temperature under a nitrogen atmosphere. After 26 hr, the resulting solution is treated with 8 g of sodium hydroxide in 40 ml of water and 40 ml of methanol, with stirring maintained under a nitrogen atmosphere. After 13 hr the suspension is acidified to pH 4 with 500 ml of 1N aqueous hydrogen chloride, then saturated with sodium chloride and extracted with four 300 ml portions of ethyl acetate. The combined ethyl aetate extracts are then washed with four 250 ml portions of 1N aqueous sodium hydroxide. The combined basic extracts are then acidified to pH 4 with concentrated hydrochloric acid, saturated with brine, and extracted with four 300 ml portions of ethyl acetate. The combined extracts are then washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to yield 22.6 g of a yellow liquid, 5-carboxypentanol, t-butyldimethylsilyl ether. Chromatography on 800 g of silica gel eluting with ethyl acetate and hexane (1:9) to 1:1) yields 14.8 g (67%) of 5-carboxypentanol, t-butyldimethylsilyl ether, which can be distioled (152° at 0.02 torr) to give a 99% yield of acid as a colorless oil (solidifies in the freezer).

Provenance & Evidence