Acetic Anhydride → HCID 13335393, compound

HRID 568760Notes

Reaction equation

HRID 568760 reaction equation
[CH2:1]([CH:4]1[C:8]([OH:10])([CH3:9])[CH:7]=[CH:6][C:5]1=[O:11])[CH:2]=[CH2:3].[C:12](OC(=O)C)(=[O:14])[CH3:13]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:12]([O:10][C:8]1([CH3:9])[CH:7]=[CH:6][C:5](=[O:11])[CH:4]1[CH2:1][CH:2]=[CH2:3])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic Anhydride2×HCID 128798724-Hydroxy-4-methyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

Product 1

HCID 13335393HCID 13335393, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

lnto a flask equipped with a stirrer and a thermometer, dl-2-allyl-3-hydroxy-3-methyl-4-cyclopentenone (152 g), p-toluenesulfonic acid (1 g) and acetic anhydride (320 g) were charged, and the resultant mixture was stirred at 100° C. for 2 hours. After completion of the reaction, acetic anhydride was removed under reduced pressure, and the residue was extracted with toluene. The toluene layer was washed with 1% sodium bicarbonate solution and water in order. Toluene was removed from the toluene layer to give dl-3-acetoxy-2-allyl-3-methyl-4-cyclopentenone (186 g). Yield, 96%. B.P., 72°-75° C./0.2-0.3 mmHg.

Workup

  1. customlnto a flask equipped with a stirrer
  2. customwas removed under reduced pressure
  3. extractionthe residue was extracted with toluene
  4. washThe toluene layer was washed with 1% sodium bicarbonate solution and water in order
  5. customToluene was removed from the toluene layer

Sources & evidence

ORD record
ord-7e487ccd5c214272ad72254cae66a837
Source dataset
uspto-grants-1988_03
Patent number
US04729953

Reaction notes

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