p-Toluenesulfonic acid → HCID 86634954, compound

HRID 1665214Notes

Reaction equation

HRID 1665214 reaction equation
[CH2:1]([O:4][N:5]=[CH:6]/[C:7](/[CH3:21])=[CH:8]/[C@@H:9]1[C@@H:11]([C:12]([O:14]C(C)(C)C)=[O:13])[C:10]1([CH3:20])[CH3:19])[CH:2]=[CH2:3].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:4][N:5]=[CH:6]/[C:7](/[CH3:21])=[CH:8]/[C@@H:9]1[C@@H:11]([C:12]([OH:14])=[O:13])[C:10]1([CH3:20])[CH3:19])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86634964HCID 86634964, compound

Product 1

HCID 86634954HCID 86634954, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under nitrogen atmosphere, a mixture of 0.74 g of t-butyl (1R)-trans-3-[(E)-3-(2-propenyloxyimino)-2-methyl-1-propenyl]-2,2-dimethylcyclopropanecarboxylate, catalytic amount of p-toluenesulfonic acid and 10 ml of toluene was stirred for 1 hour under reflux. The reaction mixture was cooled down to room temperature, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.47 g of (1R)-trans-3-[(E)-3-(2-propenyloxyimino)-2-methyl-1-propenyl]-2,2-dimethylcyclopropanecarboxylic acid:

Workup

  1. temperatureunder reflux
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b5e2078187ea44b3bc9e76cdbdc8cc81
Source dataset
uspto-grants-2011_10
Patent number
US08039499B2

Reaction notes

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