[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C[O-].[Na+].CO.[Cl:14][C:15](Cl)=[CH:16][C:17]([CH3:20])([CH3:19])[CH3:18]>CN(C)C=O.C(Cl)Cl>[Cl:14][CH:15]=[C:16]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:17]([CH3:20])([CH3:19])[CH3:18]
26 g (0.2 mol) of p-chlorophenol were reacted with 40 ml of 30% strength sodium methylate solution (0.2 mol) in 150 ml of dimethylformamide. After the methanol had been stripped off, a further 50 ml of dimethylformamide were distilled off under 20 mbar. 15.3 g (0.1 mol) of 1,1-dichloro-3,3-dimethyl-1-butene were then added and the mixture was heated under reflux for 18 hours. The solution was diluted with methylene chloride and extracted three times by shaking with dilute sodium hydroxide solution. The organic phase was dried over sodium sulphate and the solvent was removed in vacuo. Distillation gave dimethylformamide in the first runnings, and 20 g of 1-chloro-3,3-dimethyl-2-(4'-chlorophenoxy)-1-butene, that is to say 81% of theory, as the main fraction at boiling point 110°-128° C./0.15 mm Hg. NMR (CDCl3): δ 1.15 (s, 9H), 5.9 (s, 1H) and 6.8- 7.4 (m, 4H). ##STR9##
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