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

HRID 1105852Notes

Reaction equation

HRID 1105852 reaction equation
[F:1][CH:2]([F:12])[O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7].C(N(CC)CC)C.[CH3:20][C:21]1([CH3:31])[CH:23]([CH:24]=[C:25]([Cl:27])[Cl:26])[CH:22]1[C:28](Cl)=[O:29].O>C1(C)C=CC=CC=1>[CH3:20][C:21]1([CH3:31])[CH:23]([CH:24]=[C:25]([Cl:26])[Cl:27])[CH:22]1[C:28]([O:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[O:3][CH:2]([F:12])[F:1])=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94551Permethric chlorideHCID 2736992(2-(Difluoromethoxy)phenyl)methanol

Product 1

HCID 233170152-Difluoromethoxybenzyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylateYield 85.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

6.09 g (0.035 mol) of 2-difluoromethoxybenzyl alcohol and 3.5 g (0.035 mol) of triethylamine were dissolved in 50 ml of toluene and the solution was added dropwise to a mixture of 7.95 g (0.35 mol) of 2,2-dimethyl-3-(2',2'-dichloro-vinyl)-cyclopropanecarboxylic acid chloride in 100 ml of toluene at 20°-25° C. The reaction mixture was subsequently stirred at room temperature for 3 hours and poured into 150 ml of water, the toluene phase was filtered 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° C./0.2 to 1.0 mm Hg. 10.9 g (81% of theory) of 2-difluoromethoxybenzyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylate were obtained as a viscous oil with the refractive index nD20 =1.5190.

Workup

  1. filtrationthe toluene phase was filtered off
  2. washwashed with 100 ml of water
  3. dry with materialdried with sodium sulphate
  4. distillationthe toluene was distilled off in vacuo
  5. customLast residues of solvent were removed by incipient distillation at a bath temperature of 60° C./0.2 to 1.0 mm Hg

Sources & evidence

ORD record
ord-2807ec1d2c964e849364457d1c45f9b9
Source dataset
uspto-grants-1982_01
Patent number
US04310540

Reaction notes

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