Hydrochloric Acid → 1,3-Dihydroisobenzofuran

Participants

Reaction Conditions

Reaction Steps

A reagent, α,α′-dihydroxy-o-xylene, produced by Aldrich Co. (69.5 g, 0.5 mol) was placed in a 500-mL four-neck flask equipped with a condenser tube, a stirring blade, a thermometer, and a dropping funnel, and 35% hydrochloric acid (100 g, 1.0 mol) was added thereto. The mixture was stirred at 70° C. for one hour. After completion of reaction, the reaction mixture was allowed to stand, so that two-separated layers were formed. The reaction was analyzed through GC while stirring again during sampling. From the obtained concentration of α-chloro-α′-hydroxy-o-xylene, the yield of α-chloro-α′-hydroxy-o-xylene was calculated to be 91% based on α,α′-dihydroxy-o-xylene. The conversion of α,α′-dihydroxy-o-xylene was 99%, and α,α′-dichloro-o-xylene (5%) and phthalan (2%) were formed as by-products.

Provenance & Evidence