1-Butanol → HCID 22921473, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(4-nitrophenyl)butyronitrile (10.0 g), butanol (10 ml) and methyl acrylate (5.2 ml) was cooled to 10° C. in a 100 ml 3-necked round-bottomed flask, equipped with a magnetic follower. A solution of potassium tert-butoxide (0.6 g) in tert-butanol (10 ml) was added dropwise, maintaining the temperature at approximately 10° C. (solution turns purple). After addition was complete, the mixture was allowed to reach ambient temperature and then stirred for a further 2 hours. The reaction was worked-up by partitioning between diethyl ether (400 ml) and 1M KH2PO4 (400 ml). The ether layer was washed with water (50 ml), dried (MgSO4) and concentrated under reduced pressure to yield methyl 4-cyano-4-(4-nitrophenyl)hexanoate (14.1 g, 99%) as an orange oil.

Provenance & Evidence