2-Methylbenzenesulfonic acid → HCID 14071121, compound

HRID 568765Notes

Reaction equation

HRID 568765 reaction equation
[CH2:1]([CH:4]1[CH:8]([OH:9])[CH:7]=[CH:6][C:5]1=[O:10])[CH:2]=[CH2:3].C1(C)C(S(O)(=O)=O)=CC=CC=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>>[C:22]([O:10][CH:5]1[CH:6]=[CH:7][C:8](=[O:9])[CH:4]1[CH2:1][CH:2]=[CH2:3])(=[O:24])[CH3:23]

Participants

4

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 7918Acetic AnhydrideHCID 12877516HCID 12877516, compound

Product 1

HCID 14071121HCID 14071121, compound

Procedure

In a flask, dl-2-allyl-3-hydroxy-4-cyclopentenone (13.8 g), toluenesulfonic acid (0.1 g) and acetic anhydride (27.6 g) were charged, and the resultant mixture was heated at 90°-100° C. for 3 hours. The reaction mixture was treated as in Example 28 to give 16.0 g of dl-3-acetoxy-2-allyl-4-cyclopentenone. Yield, 89%. B.P., 80°-85° C./0.6-1 mmHg.

Workup

  1. additionThe reaction mixture was treated as in Example 28

Sources & evidence

ORD record
ord-dfb78c9e5fe6411fa59200d31a8a858f
Source dataset
uspto-grants-1988_03
Patent number
US04729953

Reaction notes

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