Acetone → HCID 18421468, compound

HRID 1281645Notes

Reaction equation

HRID 1281645 reaction equation
[OH:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6]([CH3:26])=[C:7]([CH2:14][N:15]3[C:19](=[O:20])[C:18]4=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]4[C:16]3=[O:25])[C:8](=[O:13])[O:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:34][C:35](=[O:37])[CH3:36].CC(C)=O>C(Cl)Cl>[CH3:26][C:6]1[C:5]2[C:10](=[C:11]([CH3:12])[C:2]([O:1][CH2:34][C:35](=[O:37])[CH3:36])=[CH:3][CH:4]=2)[O:9][C:8](=[O:13])[C:7]=1[CH2:14][N:15]1[C:16](=[O:25])[C:17]2=[CH:24][CH:23]=[CH:22][CH:21]=[C:18]2[C:19]1=[O:20]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 18421402HCID 18421402, compound

Product 1

HCID 18421468HCID 18421468, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A slurry of 7-hydroxy-4,8-dimethyl-3-phthalimidomethylcoumarin (4.00 g, 11.5 mmol), potassium carbonate (4.5 g, 36.9 mmol), chloroacetone (1 mL, 11.5 mmol) and acetone (200 mL) were refluxed overnight. After the solution was allowed to cool to room temperature, CH2Cl2 (200 mL) was added and the resulting solid was filtered off. The remaining solution was cold decolorized with charcoal and the solvent evaporated. The resulting solid was stirred with water, vacuum filtered, and washed with water. After air drying, 4,8-dimethyl-7-(2-oxo)propyloxy-3-(phthalimidomethyl)coumarin (4.06 g, 87.1% ) was obtained as an off-white solid. 1H NMR (CDCl3): δ7.66-7.83 (m, 4H), 7.48 (d, J=8.8 Hz, 1H), 6.65 (d, J=8.8 Hz, 1H), 4.91 (s, 2H), 4.62 (s, 2H), 2.59 (s, 3H), 2.35 (s, 3H), 2.32 (s, 3H).

Workup

  1. filtrationthe resulting solid was filtered off
  2. customthe solvent evaporated
  3. filtrationfiltered
  4. washwashed with water
  5. customAfter air drying

Sources & evidence

ORD record
ord-aa07ade9a9c6439789cd561a911c0da7
Source dataset
uspto-grants-2002_09
Patent number
US06455286B1

Reaction notes

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