p-Toluenesulfonic acid → (1R,cis)2,2-dimethyl-3-(2,2,2-trichloroethoxycarbonylethynyl)-cyclopropane-carboxylic acid

HRID 1995161Notes

Reaction equation

HRID 1995161 reaction equation
[CH3:1][C:2]1([CH3:22])[C@@H:4]([C:5]#[C:6][C:7]([O:9][CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])=[O:8])[C@H:3]1[C:15]([O:17]C(C)(C)C)=[O:16].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:22])[C@@H:4]([C:5]#[C:6][C:7]([O:9][CH2:10][C:11]([Cl:13])([Cl:14])[Cl:12])=[O:8])[C@H:3]1[C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 13093790tert.butyl(1R,cis)2,2-dimethyl-3-(2,2,2-trichloroethoxycarbonylethynyl)-cyclopropane-carboxylate

Product 1

HCID 13093792(1R,cis)2,2-dimethyl-3-(2,2,2-trichloroethoxycarbonylethynyl)-cyclopropane-carboxylic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 11.4 g of the product of Step A, 120 ml of toluene and 300 mg of p-toluene sulfonic acid was refluxed for one hour and was cooled to room temperature. The mixture was washed with water, dried and evaporated to dryness under reduced pressure to obtain 9.5 g of (1R,cis) 2,2-dimethyl-3-[2,2,2-trichloroethoxycarbonyl-ethynyl]-cyclopropane-carboxylic acid which used as is for the next step.

Workup

  1. temperaturewas refluxed for one hour
  2. washThe mixture was washed with water
  3. customdried
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-daf8c7e44a06446086a22feaa64b8cbd
Source dataset
uspto-grants-1983_09
Patent number
US04402972

Reaction notes

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