HCID 57190765, compound → HCID 54017022, compound

Participants

Reaction Steps

A solution of 21.8 g (0.129 mole) of the crude (5S)-5-(3-hydroxypropyl)-6-methyl-2-cyclohexene-1-one in 200 ml of EtOAc was stirred with 1.0 g 10% Pd(C) under 1 atmosphere pressure of hydrogen until a total of 2600 ml of hydrogen was consumed. The reaction mixture was then filtered through a pad of celite which was washed further with EtOAc. The combined filtrates were concentrated to give 22.0 g of the crude ketone which was chromatographed on a silica gel column (4:1, hexane/EtOAc) to give 13.5 g (50% from s-carvone) of the pure (3R)-3-(3-hydroxypropyl)-2-methycyclohexanone. B.P. 110° C./0.15 mmHg. IR (CHCl3): 1702, 3475, 3625 cm-1.

Provenance & Evidence