beta-HOMOCYCLOCITRAL → 1-Cyclohexene-1-propanal, 2,6,6-trimethyl-

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Reaction Steps

2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde is reacted with methoxymethyl triphenylphosphonium chloride in the presence of potassium tert-butoxide, followed by conversion to the dimethyl acetal and subsequent hydrolysis, as described in Example 1 above, to provide 3-(2,6,6-trimethyl-1-cyclohexen-1yl)propanal (80% yield) as a colorless oil after distillation in vacuo. This material (6.8 g) is reacted with triethyl 2-phosphonopropionate (10.6 ml) by the method of example 14(B) above, to provide 6.58 g (2E)-2-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-pentenoic acid ethyl ester as a colorless oil after chromatography. This ester is reduced with diisobutylaluminum hydride by the method described in example 14(B) above, to provide (2E)-2-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-pentenol as a colorless oil (93%) after chromatography.

Provenance & Evidence