Water → HCID 86738244, compound

HRID 1447047Notes

Reaction equation

HRID 1447047 reaction equation
[CH3:1][C:2]1([CH3:13])[C@H:4]([CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])[C@@H:3]1[C:10](Cl)=[O:11].[C:14]([CH:16]([OH:30])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:18]=1)#[N:15].N1C=CC=CC=1.O>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:13])[C@H:4]([CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])[C@@H:3]1[C:10]([O:30][CH:16]([C:14]#[N:15])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:18]=1)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 93218Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-HCID 86738245HCID 86738245, compound

Product 1

HCID 86738244HCID 86738244, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 10.0 g of cis-2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropanecarbonyl chloride in 80 ml of dry benzene, there were added first 8.5 g of α-cyano-3-phenoxybenzyl alcohol and then gradually 4.5 g of pyridine. The mixture was stirred at room temperature overnight. 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. The oily product thus obtained was purified by preparative liquid chromatography following the procedure of SYNTHESIS EXAMPLE 1 to give 12.1 g (70% yield) of α-cyano-3-phenoxybenzyl cis-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. customThe oily product thus obtained
  6. customwas purified by preparative liquid chromatography
  7. customthe procedure of SYNTHESIS EXAMPLE 1

Sources & evidence

ORD record
ord-c23e20cf89444799b259eab92137a08c
Source dataset
uspto-grants-1982_02
Patent number
US04315029

Reaction notes

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