Cyclohexene → HCID 53726874, compound

Participants

Reaction Steps

The combined product from the previous reaction (57.27 g), palladium on carbon (10%; 2.75 g), cyclohexene (81.4 ml) and ethyl acetate (2 L) were heated and stirred together under reflux under nitrogen for 24 hours. The solvent was evaporated and the residue dissolved in ethyl acetate (1 L) then filtered through a pad of Celite. The solvent was removed in vacuo to give an orange oil, which was dissolved in a mixture of ethanol (500 ml), water (500 ml) and triethylamine (55.2 ml). This mixture was stirred and heated under reflux for 3 hours. After cooling the ethanol was removed in vacuo and the remaining aqueous mixture extracted with ethyl acetate (2×250 ml). The combined extracts were washed with hydrochloric acid (1 M; 2×250 ml) then water then dried over magnesium sulphate. The solvent was removed in vacuo and the residue purified by flash chromatography over silica eluting with a 3:1, followed by a 1:1, mixture of petroleum ether (b.p. 40-60° C.) and ethyl acetate. Appropriate fractions were combined and the solvent removed in vacuo to give (S)-2-hydroxymethyl-1,4-benzodioxan-8-carboxaldehyde (8.02 g).

Provenance & Evidence