p-Toluenesulfonic acid → 2,2-Dimethyl 3-(3-isobutoxy 3-oxo-1-propenyl) cyclopropane-1-carboxylic acid

HRID 1762613Notes

Reaction equation

HRID 1762613 reaction equation
[CH3:1][C:2]1([CH3:17])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH:10]2[CH2:13][CH2:12]C2)=[O:8])[CH:3]1[C:14]([OH:16])=[O:15].[C:18]1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:17][C:2]1([CH3:1])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH2:10][CH:13]([CH3:12])[CH3:18])=[O:8])[CH:3]1[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 539623272,2-Dimethyl-3-(3-cyclobutoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid

Product 1

HCID 545483472,2-Dimethyl 3-(3-isobutoxy 3-oxo-1-propenyl) cyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into 20 cm3 of toluene are introduced 2.1 g of tertbutyl (1R cis, ΔZ) 2,2-dimethyl 3-(3-isobutoxy 3-oxo 1-propenyl) cyclopropane-1-carboxylate and 0.1 g of paratoluene sulphonic acid, the whole is taken to reflux and maintained there for 20 minutes, concentrated to dryness by distillation under reduced pressure and chromatographed on silica eluting with a mixture of hexane and ethyl acetate (7:3) containing 1% of acetic acid and 1.53 g of (1R cis, ΔZ) 2,2-dimethyl 3-(3-isobutoxy 3-oxo-1-propenyl) cyclopropane-1-carboxylic acid are obtained.

Workup

  1. temperatureto reflux
  2. temperaturemaintained there for 20 minutes
  3. concentrationconcentrated to dryness by distillation under reduced pressure
  4. customchromatographed on silica eluting with a mixture of hexane and ethyl acetate (7:3)
  5. additioncontaining 1% of acetic acid and 1.53 g of (1R cis, ΔZ) 2,2-dimethyl 3-(3-isobutoxy 3-oxo-1-propenyl) cyclopropane-1-carboxylic acid
  6. customare obtained

Sources & evidence

ORD record
ord-1870b9c9ff274c77911fec7773341652
Source dataset
uspto-grants-1989_05
Patent number
US04833163

Reaction notes

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