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Potassium Carbonate → alpha-[(6-Acetyl-2-methoxycarbonylphenyl)oxy]-gamma-butyrolactone

HRID 66585
Notes
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Reaction equation

HRID 66585 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]=1[OH:14])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH:22]1[CH2:27][CH2:26][O:25][C:23]1=[O:24]>CC(C)=O>[C:1]([C:4]1[C:5]([O:14][CH:22]2[CH2:27][CH2:26][O:25][C:23]2=[O:24])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=[CH:12][CH:13]=1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 13037297Methyl 3-acetyl-2-hydroxybenzoate

Product 1

HCID 13037298alpha-[(6-Acetyl-2-methoxycarbonylphenyl)oxy]-gamma-butyrolactone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of methyl 3-acetylsalicylate (5.8 g) and potassium carbonate (10.4 g) in acetone (200 ml) was added α-bromo-γ-butyrolactone (12.5 g) under stirring, and the mixture was refluxed for 11 hours. The insolubles were filtered off and the filtrate was concentrated under reduced pressure. The residue was subjected to chromatography on silica gel eluting with chloroform. By the above procedure, there was obtained α-[(6-acetyl-2-methoxycarbonylphenyl)oxy]-γ-butyrolactone as pale yellow oil.

Workup

  1. temperaturethe mixture was refluxed for 11 hours
  2. filtrationThe insolubles were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6d6d16c133d14dc98d2670831a546e4a
Source dataset
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04342779

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes