Acetic Anhydride → 4-(4-fluorophenyl)dihydro-2H-pyran-2,6(3H)-dione

HRID 1272273Notes

Reaction equation

HRID 1272273 reaction equation
C(OC(=O)C)(=O)C.[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:20][C:21]([OH:23])=[O:22])[CH2:16][C:17]([OH:19])=O)=[CH:11][CH:10]=1>>[F:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[CH2:16][C:17](=[O:19])[O:23][C:21](=[O:22])[CH2:20]2)=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 769903-(4-Fluorophenyl)pentanedioic acid

Product 1

HCID 111600754-(4-fluorophenyl)dihydro-2H-pyran-2,6(3H)-dioneYield 76.1%

Procedure

To acetic anhydride (5 ml) was added 3-(4-fluorophenyl)glutaric acid (2.00 g, 8.84 mmol) and the mixture was refluxed for 3 hours. The resulting mixture was concentrated under reduced pressure, and the residue was crystallized from ethyl acetate-hexane to obtain 1.4 g (yield 76%) of the title compound. mp. 99–104° C.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. concentrationThe resulting mixture was concentrated under reduced pressure
  3. customthe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-6e41fd5d137641adac5de8401eb7fe28
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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