Acetic Acid → HCID 19804623, compound

Participants

Reaction Conditions

Reaction Steps

19.5 grams of 3-allyl-2-methoxy-6,11-dihydrodibenz[b,e]oxepin-11-one obtained in the above Reference Example were dissolved in a mixed liquid consisting of 400 ml of acetone, 150 ml of acetic acid and 150 ml of water and incorporated in portions with 44 g of potassium permanganate at a temperature of 10°-15 C. over a period of 4 hours, after which the whole was agitated at 15° C. for 1 hour. After the end of the reaction, the unreacted potassium permanganate was decomposed with sodium hydrogen sulfite, after which the insoluble materials in the reaction mixture were filtered out and then the filtrate obtained was evaporated to dryness under a reduced pressure. The residue obtained was incorporated with water to precipitate crystals which were then filtered off. The crystals so filtered off were adsorbed in silica gel packed in a column and developed with a 7:1 chloroform-methanol mixed solution (silica gel column chromatography). The resulting effluent was freed from the solvent by distillation, after which the residue obtained was recrystallized from ethyl acetate thereby to obtain 5.6 g of 2-methoxy-6,11-dihydro-11-oxodibenz[b,e]oxepin-3-acetic acid in the form of colorless needle-like crystals.

Provenance & Evidence