p-Toluenesulfonic acid → HCID 70476476, compound

HRID 464454Notes

Reaction equation

HRID 464454 reaction equation
[CH3:1][C:2]1([CH3:21])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:8])[C@H:3]1[C:14]([O:16]C(C)(C)C)=[O:15].C1(C)C=CC(S(O)(=O)=O)=CC=1.CC(=C)C>C1(C)C=CC=CC=1>[CH3:21][C:2]1([CH3:1])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:8])[C@H:3]1[C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8255IsobutyleneHCID 86740372HCID 86740372, compound

Product 1

HCID 70476476HCID 70476476, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3.3 g of the product of Step B, 350 mg of p-toluene sulfonic acid and 40 ml of toluene was stirred at reflux until isobutylene evolution ceased (about 40 minutes) and was then evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 75-25-1 cyclohexane-ethyl acetate-acetic acid mixture to obtain 2 g of (1R,cis)2,2-dimethyl-3-[Z-2-(n-butoxycarbonyl)-ethenyl]-cyclopropane-carboxylic acid.

Workup

  1. custom(about 40 minutes)
  2. customwas then evaporated to dryness under reduced pressure
  3. customThe residue was chromatographed over silica gel
  4. washwas eluted with a 75-25-1 cyclohexane-ethyl acetate-acetic acid mixture

Sources & evidence

ORD record
ord-5019e5e794a24fd480f998b617c558d8
Source dataset
uspto-grants-1985_10
Patent number
US04547522

Reaction notes

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