1,1-dichloro-3,3-dimethylbut-1-ene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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## a further 50 ml of dimethylformamide were distilled off under 20 mbar the mixture was heated under reflux for 18 hours extracted three times The organic phase was dried over sodium sulphate the solvent was removed in vacuo Distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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## a further 50 ml of dimethylformamide were distilled off under 20 mbar the mixture was heated under reflux for 18 hours extracted three times The organic phase was dried over sodium sulphate the solvent was removed in vacuo Distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Analogously to Example A6(a), 0.2 mol of 3-methylphenol and 0.1 mol of 1,1-dichloro-3,3-dimethyl-1-butene are reacted to give 19.6 g of 1-chloro-3,3-dimethyl-2-(3'-methylphenoxy)-1-butene of boiling point 95°-100° C./0.7 mm Hg. The yield is 87% of theory.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 16.5 g (0.108 mols) of 1,1-dichloro-3,3-dimethyl-1-butene are heated under reflux with 23.2 g (0.2 mol) of sodium phenolate in 100 ml of dimethylformamide, during the course of 12 hours. The customary working-up according to Example A1(a) yields, with distillation at a boiling point of 80° C./0.5 mm Hg, 22.3 g of 1-chloro-3,3-dimethyl-2-phenoxy-1-butene.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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## a further 50 ml of dimethylformamide were distilled off under 20 mbar the mixture was heated under reflux for 18 hours extracted three times The organic phase was dried over sodium sulphate the solvent was removed in vacuo Distillation