HCID 15044953, compound → HCID 15044954, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of α,α'-bis(3,4,5-trimethoxyphenyl)adipic acid (10 g, 21 mmoles) and acetic anhydride (30 ml) was heated at 150° C. for 30 minutes. Acetic acid and anhydride were removed in vacuo. The flask containing the solid residue was fitted with a distillation head and while under vacuum (~150 mm) was placed in an oil bath heated to 287° C. The solid melted; there was a vigorous evolution of gas and about 5 ml of liquid distilled. After 6.5 minutes the flask was cooled rapidly with a water bath. The yellow-brown syrupy residue was dissolved in 80 ml of hot ethanol, filtered from some insoluble material and seeded. After standing at room temperature overnight, the crystalline solid was filtered, washed with cold ethanol (3 times) and dried to give 5.57 g (64%) of trans-2,5-bis(3,4,5-trimethoxyphenyl)cyclopentanone, m.p. 140°-142.5°. IR 1740 cm-1 (C=O), mass spec m/e 416 (M+).

Provenance & Evidence