Water → HCID 86738246, compound

HRID 1447048Notes

Reaction equation

HRID 1447048 reaction equation
[C:1]([CH:3]([OH:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=1)#[N:2].[CH3:18][C:19]1([CH3:30])[C@@H:21]([CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])[C@@H:20]1[C:27](Cl)=[O:28].N1C=CC=CC=1.O>C1C=CC=CC=1>[CH3:18][C:19]1([CH3:30])[C@@H:21]([CH2:22][C:23]([Cl:24])([Cl:25])[Cl:26])[C@@H:20]1[C:27]([O:17][CH:3]([C:1]#[N:2])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=1)=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 93218Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-HCID 86738247HCID 86738247, compound

Product 1

HCID 86738246HCID 86738246, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

α-Cyano-3-phenoxybenzyl alcohol (8.5 g) was added to a solution of 10.0 g of trans-2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropanecarbonyl chloride in 80 ml of dry benzene, then 4.5 g of pyridine was added gradually and the mixture was stirred at room temperature overnight. Thereafter, about 70 ml of water was added to the reaction mixture, the benzene layer was separated, washed with water and dried over anhydrous magnesium sulfate, and low-boiling fractions were distilled off under reduced pressure. There was obtained an oily product, which was purified by preparative liquid chromatography under the conditions mentioned in SYNTHESIS EXAMPLE 25 to give 13.3 g (77% yield) of α-cyano-3-phenoxybenzyl trans-2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropanecarboxylate with a ratio of racemic modifications D1 '/D2 ' of about 50/50.

Workup

  1. customthe benzene layer was separated
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate, and low-boiling fractions
  4. distillationwere distilled off under reduced pressure
  5. customThere was obtained an oily product, which
  6. customwas purified by preparative liquid chromatography under the conditions
  7. custommentioned in SYNTHESIS EXAMPLE 25

Sources & evidence

ORD record
ord-40417910e9084292bc94d88b0e16dcf7
Source dataset
uspto-grants-1982_02
Patent number
US04315029

Reaction notes

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