Ethyl chloroacetate → HCID 53893019, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of geranylgeranylacetone (32.2 g) and ethyl monochloroacetate (17.2 g), sodium ethoxide (8.85 g) is portionwise added at -10°C in nitrogen stream. The resultant mixture is stirred for 7 hours, a solution of potassium hydroxide (99 g) in methanol (560 ml) is added thereto, stirring is continued for 3 hours and then the resulting mixture is allowed to stand overnight. Then, the reaction mixture is poured into water, washed with petroleum ether, neutralized with acetic acid and extracted with ether. The ether extract is washed with water, dried and evaporated. The residue is heated at 150°C for 30 minutes for decarboxylation. The resulting crude produce (31 g) is purified by chromatography on silica gel (300 g) using benzene to give 2,6,10,14,18-pentamethyl-5,9,13,17-nonadecatetraenal (23.8 g). IR: 2680, 1720 cm-1 (CHO).

Provenance & Evidence