Hydrochloric Acid → 3-Phenylpentane-1,5-diol

Participants

Reaction Steps

3.0 g (14.4 mmol) of 3-phenylglutaric acid were dissolved in 20 ml of abs. THF, the mixture was cooled to −10° C. and 31.7 ml (31.7 mmol) of a 1 M solution of lithium aluminium hydride in THF were added dropwise. During the addition, a further 50 ml of abs. THF were added. The resulting suspension was slowly warmed to RT and stirred at RT overnight. After cooling to 0° C., initially isopropanol and then a mixture of isopropanol and water (3:1) were carefully added dropwise. The resulting suspension was acidified by addition of 1 N hydrochloric acid and mixed with Celite. The mixture was filtered through Celite, the filter cake was washed with isopropanol and the filtrate obtained was concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 2:1→1:1). This gave 1.9 g of the target product (73% of theory).

Provenance & Evidence