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

HRID 1762618Notes

Reaction equation

HRID 1762618 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][CH2:11]2)=[O:8])[CH:3]1[C:14]([OH:16])=[O:15].C1(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]2[CH2:12][CH2:11]2)=[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 539155962,2-Dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl) cyclopropane-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 12.32 g of the product of Step A, 0.6 g of p-toluene sulfonic acid and 120 ml of toluene was refluxed for 45 minutes and was cooled and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 7-3 n-hexane-ethyl acetate mixture containing 1% o acetic acid to obtain 8.94 g of (1R, cis, ΔZ) 2,2-dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl) cyclopropane-carboxylic acid melting at 106° C.

Workup

  1. temperaturewas refluxed for 45 minutes
  2. temperaturewas cooled
  3. customevaporated to dryness under reduced pressure
  4. customThe residue was chromatographed over silica gel
  5. washwas eluted with a 7-3 n-hexane-ethyl acetate mixture
  6. additioncontaining 1% o acetic acid

Sources & evidence

ORD record
ord-e966886adaf1485e8414f340671b5989
Source dataset
uspto-grants-1989_05
Patent number
US04833163

Reaction notes

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