Ethylene Glycol → 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid methyl ester

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Reaction Steps

1.1 Gm. of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid methyl ester is stirred in 10 ml. of benzene containing 0.9 gm. of phosphorus pentachloride for one hour. The solution is then added to a stirred, ice cooled mixture of 2.4 ml. of ethylene glycol, 2.5 ml. of triethylamine, and 13 ml. of acetonitrile. The mixture is allowed to attain room temperature, and then water and ether are added. The ethereal layer is washed several times with water, then dried and evaporated to give a quantitative yield of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid methyl ester. Use of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetic acid methyl ester gives a similar yield of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)acetic acid methyl ester.

Provenance & Evidence