Water → 3-Difluoromethoxy-benzyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylate

HRID 1105853Notes

Reaction equation

HRID 1105853 reaction equation
[F:1][CH:2]([F:12])[O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br.[CH3:13][C:14]1([CH3:24])[CH:16]([CH:17]=[C:18]([Cl:20])[Cl:19])[CH:15]1[C:21]([OH:23])=[O:22].[OH-].[K+].O>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:13][C:14]1([CH3:24])[CH:16]([CH:17]=[C:18]([Cl:20])[Cl:19])[CH:15]1[C:21]([O:23][CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([O:3][CH:2]([F:12])[F:1])[CH:5]=1)=[O:22]

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 91658Permethric acidHCID 27369993-(Difluoromethoxy)benzyl bromide

Product 1

HCID 233170343-Difluoromethoxy-benzyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

6.81 g (0.03 mol) of 3-difluoromethoxy-benzyl bromide and 6.27 g (0.03 mol) of 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylic acid were dissolved in 150 ml of toluene, 0.5 g of tetrabutylammonium bromide and 2 g of powdered KOH (industrial product, 87% pure) were added and the mixture was heated to the boil for 2-3 hours. After cooling, the reaction mixture was poured into 150 ml of water, the toluene phase was separated off, washed with 100 ml of water and dried with sodium sulphate and the toluene was distilled off in vacuo. Last residues of solvent were removed by incipient distillation at a bath temperature of 60°-80° C./0.2 to 1 mm Hg. 8.3 g (78% of theory) of 3-difluoromethoxy-benzyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylate were obtained as a viscous oil with the refractive index hD20 =1.5110.

Workup

  1. temperaturethe mixture was heated to the boil for 2-3 hours
  2. temperatureAfter cooling
  3. customthe toluene phase was separated off
  4. washwashed with 100 ml of water
  5. dry with materialdried with sodium sulphate
  6. distillationthe toluene was distilled off in vacuo
  7. customLast residues of solvent were removed by incipient distillation at a bath temperature of 60°-80° C./0.2 to 1 mm Hg

Sources & evidence

ORD record
ord-cdb1b75c75cc4090a610983e6f6dd6d0
Source dataset
uspto-grants-1982_01
Patent number
US04310540

Reaction notes

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