Chloroacetone → 4,6-Dimethyl-7-acetonyloxycoumarin

HRID 1646425Notes

Reaction equation

HRID 1646425 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:13])=[C:9]([CH3:12])[CH:10]=2)[O:5][C:4](=[O:14])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:22][C:23](=[O:25])[CH3:24]>CC(C)=O>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:13][CH2:22][C:23]([CH3:24])=[O:25])=[C:9]([CH3:12])[CH:10]=2)[O:5][C:4](=[O:14])[CH:3]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 107977397-Hydroxy-4,6-dimethyl-2H-1-benzopyran-2-one

Product 1

HCID 545237254,6-Dimethyl-7-acetonyloxycoumarin

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4,6-dimethyl-7-hydroxycoumarin (III) (5.0 g), anhydrous K2CO3 (10 g), chloroacetone (2.5 ml) and acetone (150 ml) was refluxed for 12 h under stirring. From the refluxed mixture the solid was filtered and washed several times with acetone. The acetonic solution and the pooled washings were concentrated to dryness and the residue crystallized from MeOH, yielding 4,6-dimethyl-7-acetonyloxycoumarin (XXXVII) (5.1 g; m.p. 190° C.) ##STR42##

Workup

  1. temperaturewas refluxed for 12 h
  2. filtrationFrom the refluxed mixture the solid was filtered
  3. washwashed several times with acetone
  4. concentrationThe acetonic solution and the pooled washings were concentrated to dryness
  5. customthe residue crystallized from MeOH

Sources & evidence

ORD record
ord-066564c5ac8b4bfbaff2caa5d36ec86d
Source dataset
uspto-grants-1993_01
Patent number
US05179217

Reaction notes

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