Farnesol → (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal

Participants

Reaction Steps

To a stirred solution of 15 g of PCC in 250 mL of dichloromethane was added 10 g of (E,E)-farnesol (1). The reaction mixture was stirred at room temperature overnight and filtered through a 55-cm (height) by 5-cm (diameter) column of silica gel. The eluate was dried over MgSO4, and the solvent was removed by rotary evaporation to give a greenish-yellow oil. The crude farnesal was purified by column chromatography (silica gel/chloroform) to yield 7.25 g of product 2, predominantly the (E,E)-isomer. 1H NMR δ (ppm) 10.0 (d, CHO), 5.9 (d, CH2C(CH3)═CHCO), 5.1 (t, CH3C(CH3)═CH and CH2C(CH3)═CH), 2.3 (m, CH2C(CH3)═CH—CO), 2.5 (m, CH2C(CH3)═CHCH2CH2), 2.2 (s, CH3C═CH—CO), 2.0 (m, CH3C(CH3)═CHCH2CH2), 1.6-1.7 (all s, CH3C(CH3)═CHCH2CH2CCH3).

Provenance & Evidence