Pyridine → 2,2-Dimethyl-3-(2,2-dichlorovinyl)-cyclopropanecarboxylic acid-3-(phenoxy)-alpha-vinylbenzyl ester

HRID 1856471Notes

Reaction equation

HRID 1856471 reaction equation
N1C=CC=CC=1.[O:7]([C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[CH:17]([OH:20])[CH:18]=[CH2:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:24][C:25]1([CH3:35])[CH:27]([CH:28]=[C:29]([Cl:31])[Cl:30])[CH:26]1[C:32](Cl)=[O:33]>C1C=CC=CC=1>[O:7]([C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[CH:17]([O:20][C:32]([CH:26]1[CH:27]([CH:28]=[C:29]([Cl:30])[Cl:31])[C:25]1([CH3:35])[CH3:24])=[O:33])[CH:18]=[CH2:19])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 94551Permethric chlorideHCID 129613931-(3-Phenoxyphenyl)prop-2-en-1-ol

Product 1

HCID 129613922,2-Dimethyl-3-(2,2-dichlorovinyl)-cyclopropanecarboxylic acid-3-(phenoxy)-alpha-vinylbenzyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

3.2 g of pyridine in 10 ml of benzene is added dropwise at 5° C. to a solution of 8 g of 3-phenoxy-α-vinyl-benzyl alcohol in 30 ml of benzene, and at 10° C. is subsequently added 8 g of 2,2-dimethyl-3-(dichlorovinyl)-cyclopropanecarboxylic acid chloride. The reaction mixture is stirred for two hours at room temperature and is then allowed to stand for 12 hours. In further processing, the reaction mixture is diluted with ice water, the organic phase is extracted 3 times with 100 ml of 3% HCl solution each time and 3 times with 100 ml of 3% sodium bicarbonate solution each time; it is dried over sodium sulfate, and the benzene is distilled off. There is obtained the compound of the formula ##STR7## as colourless oil have a refractive index of nD40 =1.5710. (isomeric mixture 40% cis and 60% trans compound)

Workup

  1. customat 10° C.
  2. waitto stand for 12 hours
  3. extractionthe organic phase is extracted 3 times with 100 ml of 3% HCl solution each time and 3 times with 100 ml of 3% sodium bicarbonate solution each time
  4. dry with materialit is dried over sodium sulfate
  5. distillationthe benzene is distilled off
  6. customThere is obtained the compound of the formula ##STR7## as colourless oil

Sources & evidence

ORD record
ord-f3e6e348d20e41b79f7c7c7d630c0856
Source dataset
uspto-grants-1980_08
Patent number
US04219564

Reaction notes

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