Dichloromethane → 5-Pentyl-2,4-decadienoic acid methyl ester

Participants

Reaction Steps

As described in Example 99, 3-pentyl-2-octenal (7.85 g) was treated with (carbomethoxymethylene)triphenylphosphorane (15.3 g) in carbon tetrachloride (100 mL) containing dichloromethane (50 mL) for 3 days at room temperature. The usual work up furnished 10.1 g of 5-pentyl-2,4-decadienoic acid methyl ester which was then saponified in a refluxing mixture of methanol (40 mL) and 2N NaOH (30 mL). After 1 hour the acid was isolated in the usual way to give 8.15 g of 5-pentyl-2,4-decadienoic acid as an oil.

Provenance & Evidence