p-Toluenesulfonic acid → HCID 44562749, compound

HRID 1732435Notes

Reaction equation

HRID 1732435 reaction equation
C(OC([C:8]1([CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH3:23])[C:12](=[O:13])[CH:11]=[CH:10][CH:9]1[CH2:14][C:15]([O:17][CH3:18])=[O:16])=O)(C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH3:18][O:17][C:15]([CH2:14][CH:9]1[CH:8]([CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH3:23])[C:12](=[O:13])[CH:11]=[CH:10]1)=[O:16]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 70583183HCID 70583183, compound

Product 1

HCID 44562749HCID 44562749, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A 540 mg quantity of 5-tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone and 10 mg of p-toluene sulfonic acid are dissolved in 20 ml of benzene, and the solution is refluxed for 20 minutes. The resulting reaction mixture is neutralized with sodium bicarbonate. The solvent is distilled off from the mixture, and the residue is distilled in a vacuum, giving 4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone (compound (1-a), R2 =CH3) in a yield of 91%, b.p. 88°-92° C./2.5 mm Hg.

Workup

  1. temperaturethe solution is refluxed for 20 minutes
  2. customThe resulting reaction mixture
  3. distillationThe solvent is distilled off from the mixture
  4. distillationthe residue is distilled in a vacuum

Sources & evidence

ORD record
ord-25bc667b2d7044aaa2fde8596d3e6644
Source dataset
uspto-grants-1980_12
Patent number
US04237308

Reaction notes

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