Cl.Cl[CH2:3][C:4]1[C:5]([CH2:10][OH:11])=[CH:6][CH:7]=[CH:8][CH:9]=1.OCC1C(CO)=CC=CC=1.ClCC1C(CCl)=CC=CC=1>>[CH2:3]1[O:11][CH2:10][C:5]2[C:4]1=[CH:9][CH:8]=[CH:7][CH:6]=2A 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.
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