[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.C[Li].[C:28](=[O:30])=[O:29]>C(OCC)C.O>[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:9]=1[C:28]([OH:30])=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
To a mixture of 11 parts of 1,3-diphenoxybenzene and 40 parts of tetrahydrofuran is added 1 part of methyllithium (as a 1.82 M solution in diethyl ether) while the mixture is cooled in an ice bath. The resulting solution is heated under reflux for 2 hours and then is poured slowly onto 500 parts of dry ice. After the mixture has warmed to room temperature, 100 parts of water are added, and the tetrahydrofuran is evaporated. After the aqueous solution is extracted with 50 parts diethyl ether, it is then acidified with concentrated hydrochloric acid. The white solid which forms is collected to yield 12 parts of 2,6-diphenoxybenzoic acid. The compound is purified by recrystallization from acetonitrile to give 8 parts of pure material, M.P. 164°-165°.
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