Acetic Acid → 6-(7-Hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-7-carbaldehyde

Participants

Reaction Steps

A solution of diisobutylaluminium hydride (53 g.) in dry benzene (145 ml.) was added, with rapid stirring, to a solution of 7-cyano-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane (43.2 g.) in dry diethyl ether (432 ml.) at 10°-15° C. Stirring at ambient temperature was continued for 11/2 hours and the mixture was added to 2 N aqueous acetic acid (1 liter) at a temperature lower than 15° C. The organic phase was separated and the aqueous layer was extracted with diethyl ether. The combined organic phases were washed with aqueous sodium bicarbonate, dried over sodium sulphate, the solvents removed in vacuo and the residue distilled under reduced pressure to give 7-formyl-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane (25.3 g.), b.p. 164°-200° C./0.04-0.05 mm.Hg, νmax. 1710 cm-1, 2700 cm-1 (liquid film).

Provenance & Evidence