[OH:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][CH3:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1.Cl>ClCC(Cl)(Cl)Cl>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][CH3:12])=[CH:7][C:3]=1[C:4]([C:16]1[S:15][C:14]([CH3:13])=[CH:18][CH:17]=1)=[O:5]2-Hydroxy-5-ethylbenzoyl chloride (6.08g, 0.036 mol) and 2-methylthiophene were mixed together in tetrachloroethane (20 ml), and stannic chloride (18.78g, 0.072 mol) in tetrachloroethane (20 ml) was added dropwise with stirring, the temperature of the mixture being at about 20° C. by cooling with an ice bath. The mixture was then stirred at room temperature for 3 hours and left to stand at room temperature overnight. The resulting pink solution was poured into ice and concentrated hydrochloric acid (10 to 20 ml), stirred until the ice had melted and extracted with chloroform. The chloroform extract was washed firstly with a saturated solution of sodium bicarbonate and secondly with a saturated solution of sodium chloride, was dried (over Na2SO4), filtered and evaporated to leave an oil which distilled to give the pure title product (4.36g), bp 133°-136° C./0.1 mm, nD21 1.6341.
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