p-Toluenesulfonic acid monohydrate → HCID 86739819, compound

HRID 1154414Notes

Reaction equation

HRID 1154414 reaction equation
[CH3:1][C:2]1([CH3:19])[C@@H:4](/[CH:5]=[C:6](/[Br:11])\[C:7](=[O:10])[O:8][CH3:9])[C@H:3]1[C:12]([O:14]C(C)(C)C)=[O:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:19])[C@@H:4](/[CH:5]=[C:6](/[Br:11])\[C:7](=[O:10])[O:8][CH3:9])[C@H:3]1[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86739820HCID 86739820, compound

Product 1

HCID 86739819HCID 86739819, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3.4 g of the product of Step A, 30 ml of toluene, 0.35 g of p-toluene sulfonic acid monohydrate was refluxed until gas evolution ceased and was then cooled to 0° C. and was filtered. The filter was washed with cold toluene and the filtrate was evaporated to dryness at 40° C. under reduced pressure to obtain 2.8 g of (1R,cis) 2,2-dimethyl-3(E)-[2-bromo-3-oxo-3-methoxy-propenyl]-cyclopropane-1-carboxylic acid.

Workup

  1. filtrationwas filtered
  2. washThe filter was washed with cold toluene
  3. customthe filtrate was evaporated to dryness at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-d8bd07fd873948ff88748708eccf929e
Source dataset
uspto-grants-1984_12
Patent number
US04489093

Reaction notes

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