Acetate → HCID 20277071, compound

Participants

Reaction Steps

To a stirred mixture of 2,3,5-trimethyl-6-(6'-acetoxy-1'-oxohexyl)-1,4-benzoquinone (formula IV-1 wherein R=H3C, n=4, in the form of acetate) (0.5 part), sodium hydrosulfite (1 part) and 30% aqueous methanol (20 volume parts) was added dropwise 2 N aqueous sodium hydroxide (1.6 volume part) at 5° C. The mixture was allowed to stand for 3 hours at the same temperature. After removal of the methanol and acidification with phosphoric acid, the product was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was subjected to chromatography on silica gel and eluted with ethyl acetate to give 2,3,5-trimethyl-6-(6'-acetoxy-1'-oxohexyl)hydroquinone. (formula III-1 wherein R=H3C, X=Y=OH, n=4, in the form of acetate) (0.075 part). Further solution with the same solvent gave 2,3,5-trimethyl-6-(6'-hydroxy-1'-oxohexyl)-hydroquinone. (formula III-1 wherein R=H3C, X=Y=OH, n=4, in the free form) (0.265 part).

Provenance & Evidence