(5-Carboxypentyl)triphenylphosphanium bromide → 14-Hydroxy-7-methyl-pentadec-6-enoic acid

Participants

Reaction Steps

325 g (0.7 mol) of (5-carboxypentyl)triphenylphosphonium bromide were dissolved in 1500 ml of tetrahydrofuran. After the addition of 180 g (1.6 mol) of potassium t-butylate in 700 ml of tetrahydrofuran the mixture was treated with 175 g (0.71 mol) of 9-hydroxy-2-decanone (70% purity). After usual work up 186 g of crude 14-hydroxy-7-methyl-pentadec-6-enoic acid were obtained. This product was dissolved in 400 ml of methanol and, after the addition of 5 ml of concentrated sulphuric acid, heated to reflux for 2 hours. After work up, bulb-tube distillation and chromatography 102 g (50%) of methyl 14-hydroxy-7-methyl- pentadec-6-enoate were obtained having the following characteristics:

Provenance & Evidence