Hexahydrophthalic anhydride, cis- → (3Ar,7as)-hexahydro-2-benzofuran-1(3h)-one

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Reaction Steps

With stirring and ice-cooling, 80 ml of a solution of cis-cyclohexane-1,2-dicarboxylic anhydride (15.4 g, 100 mmol) in THF are added over a period of 10 min to a mixture of sodium borohydride (3.8 g, 100 mmol) in 20 ml of THF. The ice-bath is removed and the mixture is stirred for 2 h. 40 ml of 6 N hydrochloric acid are added carefully and the mixture is concentrated. 200 ml of water are added and the aqueous phase is extracted with ether. The organic phase is dried, filtered, concentrated and distilled under reduced pressure (123° C., 13 mm; 75° C., 0.5 mm).

Provenance & Evidence