p-Anisoyl chloride → HCID 67863489, compound

Participants

Reaction Steps

The methyl 3-(4-methoxyphenyl)propionate (10.8 g, 55.6 mmol) prepared in Example 1 and 4-methoxybenzoyl chloride (11.4 g, 66.8 mmol) were dissolved in nitrobenzene (200 ml). To the ice-chilled solution, A1C13 (26.7 g, 200.3 mmol) was added in 6 portions with vigorous stirring over a period of 3 hours. After all portions of A1C13 were added, stirring was continued for an additional 1 hour. The reaction mixture was poured into a beaker containing a mixture of ice and 120 ml of 1N CHl and stirred vigorously. The mixture was transferred into a separating funnel, which was shaken well after the addition of ethyl acetate. The organic layer in the solution was washed twice with a saturated aqueous solution of sodium bicarbonate, then twice with a saturated aqueous solution of sodium chloride. After drying over unhydrous sodium sulfate, the solvent was removed in vacuo. The residue was purified by flash column chromatography using 30% ethyl acetate/hexane to produce a pale yellow oil.

Provenance & Evidence