HCID 86740311, compound → HCID 13390089, compound

HRID 1719738Notes

Reaction equation

HRID 1719738 reaction equation
[CH3:1][C:2]1([CH3:23])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:15])[O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@H:3]1[C:16]([O:18]C(C)(C)C)=[O:17]>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:23])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:15])[O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@H:3]1[C:16]([OH:18])=[O:17]

Participants

3

Reactant 1

HCID 86740311HCID 86740311, compound

Product 1

HCID 13390089HCID 13390089, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3.3 g of the product of Step B, 35 ml of toluene and 100 mg of monohydrated p-toluene sulfonic acid was refluxed until gas evolution ceased and then was evaporated to dryness under reduced pressure. The 3.4 g residue were chromatographed over silica gel and eluted with a 70-30-1 cyclohexane-ethyl acetate acetic acid mixture to obtain 2.4 g of (1R,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-phenoxyl-propenyl]-cyclopropane-carboxylic acid melting at 57° C.

Workup

  1. temperaturewas refluxed until gas evolution
  2. customwas evaporated to dryness under reduced pressure
  3. customThe 3.4 g residue were chromatographed over silica gel
  4. washeluted with a 70-30-1 cyclohexane-ethyl acetate acetic acid mixture

Sources & evidence

ORD record
ord-fc52d3c464c54f04807d5c8db08e8f5e
Source dataset
uspto-grants-1985_09
Patent number
US04542142

Reaction notes

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