Acetic Anhydride → 2,6-dioxo-3,6-dihydro-2H-pyran-4-yl acetate

HRID 1627914Notes

Reaction equation

HRID 1627914 reaction equation
[CH2:1]([C:8]([OH:10])=[O:9])[C:2]([CH2:4][C:5]([OH:7])=O)=[O:3].[C:11](OC(=O)C)(=[O:13])[CH3:12]>C1(C)C=CC=CC=1>[C:11]([O:7][C:5]1[CH2:4][C:2](=[O:3])[O:1][C:8](=[O:9])[CH:10]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 68328Acetonedicarboxylic acid

Product 1

HCID 124390722,6-dioxo-3,6-dihydro-2H-pyran-4-yl acetateYield 54.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
35 °C

Procedure

Acetone-1,3-dicarboxylic acid (30 g; 205 mmol) was added in portions to acetic anhydride (55 ml; 582 mmol) and the mixture was stirred at 35° C. for 24 h. The reaction mixture was diluted with toluene (200 ml) and kept at 4° C. for 3 h. A precipitate was isolated by filtration, washed with toluene and dried under reduced pressure to furnish 18.91 g (54%) of 2,6-dioxo-3,6-dihydro-2H-pyran-4-yl acetate as a light brown solid.

Workup

  1. waitkept at 4° C. for 3 h
  2. customA precipitate was isolated by filtration
  3. washwashed with toluene
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-d5da928a493b47d0af25899e82902274
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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