[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]=[C:12](C(O)=O)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=1)[CH3:2].C(=O)=O.C1(C)C=CC=CC=1>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=1)[CH3:2]1 g of copper powder was added to 13 g (0.044 mol) of 3-(2-carboxy-2-phenyl-vinyl)-benzoic acid ethyl ester, dissolved in 100 ml of quinoline, and the mixture was heated to 220° C., whilst stirring, until no further evolution of carbon dioxide could be observed (about 1 hour). The mixture was then cooled immediately to room temperature. After adding 300 ml of toluene to the reaction mixture, it was extracted by shaking twice with 100 ml of concentrated hydrochloric acid each time and then washed with 500 ml of water. The organic phase was separated off and dried over magnesium sulphate, the solvent was distilled off under a waterpump vacuum and the residue was distilled in vacuo. 10 g (90.2% of theory) of 3-(2-phenyl-vinyl)-benzoic acid ethyl ester were obtained as a yellow oil with the boiling point 165°-170° C./2 mm Hg (isomer mixture with a cis proportion of about 90%). ##STR61##
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