Catechol → HCID 15471313, compound

Participants

Reaction Steps

A mixture of 10.7 g of catechol, 17.3 g of catechol diacetate, 34.5 g of potassium carbonate, 30.3 g of allyl bromide and 200 ml of acetone was refluxed for 5 hours. The reaction mixture was filtered, and the filtrate was concentrated and purified by column chromatography to give 26.5 g (yield 71%) of 2-acetoxyphenyl allyl ether as a pale yellow liquid. Ten grams of this liquid was heated at 220° to 230° C. for 1.5 hours. After cooling, the reaction mixture was purified by column chromatography to give 6.5 g (yield 65%) of 2-acetoxy-6-allylphenol as a pale yellow liquid. Then, 3.0 g of this liquid and 12 ml of an acetic acid solution of 25% hydrobromic acid were reacted at 70° C. for 6 hours. The reaction mixture was poured into ice water, neutralized with an aqueous solution of sodium bicarbonate, and extracted with ethyl acetate. The concentrate was hydrolyzed with potassium hydroxide and aqueous ethanol, and worked up in a customary manner. The product was then purified by column chromatography to give 0.7 g (yield 31%) of the desired product as a pale yellow liquid.

Provenance & Evidence