Water → 1,2-Benzenedimethanol

Participants

Reaction Conditions

Reaction Steps

Into a four-neck flask provided with a reflux condenser, thermometer, dropping funnnel, and stirrer, were charged 40 parts of o-xylylene dichloride of 99.8% purity, 40 parts of anhydrous sodium acetate, and 20 parts of monochlorobenzene. Into the flask was added with stirring at 100° C., 0.8 part of triethylamine. Esterification was allowed to proceed at 97° to 101° C. for 10 hours. To the reaction mixture was added 100 parts of warm water to dissolve the by-product sodium chloride. The mixture was left standing to allow it to settle in monochlorobenzene layer and aqueous layer. To the monochlorobenzene layer which had been freed from the catalyst amine by removing with 2.6 parts of 30-% sulfuric acid, were added 19.4 parts of sodium hydroxide and 170 parts of water. Saponification was allowed to proceed at 94° C. for 2 hours. After saponification, the reaction mixture was neutralized with 3N hydrochloric acid and left standing at 85° C. to allow the mixture to settle in two layers. Without having been freed from impurities, the aqueous layer containing o-xylylene glycol was extracted three times with ethyl acetate in a manner similar to that in Example 1. The ethyl acetate extracts were combined, distilled to recover ethyl acetate, and dried in vacuo to obtain 29.6 parts of o-xylylene glycol (melting point, 60.7° - 62° C.) in a yield of 94.0%.

Provenance & Evidence