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

HRID 569521Notes

Reaction equation

HRID 569521 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 B, 120 ml of toluene and 300 mg of p-toluene sulfonic acid was refluxed for 1 hour and was allowed to return to room temperature. The reaction mixture was washed with water, dried and evaporated to dryness to obtain 9.5 g of (1R,cis)2,2-dimethyl-3-(2,2,2-trichloroethoxycarbonylethynyl)-cyclopropane-carboxylic acid which was used as is for the following step.

Workup

  1. temperaturewas refluxed for 1 hour
  2. customto return to room temperature
  3. washThe reaction mixture was washed with water
  4. customdried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-318696df93484951a21125b0c4f26b94
Source dataset
uspto-grants-1988_03
Patent number
US04732903

Reaction notes

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