Sodium Acetate → 6-Methoxy-2-methyl-3-phenyl-4H-chromen-4-one

HRID 239614

Reaction equation

HRID 239614 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10](=[O:18])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:19]([O-])(=O)[CH3:20].[Na+]>C(OC(=O)C)(=O)C>[CH3:9][O:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[O:1][C:19]([CH3:20])=[C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:10]2=[O:18]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 27756071-(2-Hydroxy-5-methoxyphenyl)-2-phenylethanone

Product 1

HCID 665791676-Methoxy-2-methyl-3-phenyl-4H-chromen-4-oneYield 68.2%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Intermediate 20 (4 g, 16.51 mmoles) was taken in a RB flask and to this acetic anhydride (40 ml) and sodium acetate (9.48 g, 115.57 mmoles) were added and the mixture was refluxed for 12 h. After cooling to RT, the reaction mixture was quenched by the addition of ice cold water. The solid formed was filtered and washed with water. The product was dried under vacuum to afford the title compound as yellow solid (3 g, 68% yield). 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 7.60(d, J=3.0 Hz, 1H), 7.45(t, J=7.1 Hz, 2H), 7.37(m, 2H), 7.29(m, 3H), 3.89(s, 3H).2.31(s, 3H).

Workup

  1. additionwere added
  2. temperaturethe mixture was refluxed for 12 h
  3. customthe reaction mixture was quenched by the addition of ice cold water
  4. customThe solid formed
  5. filtrationwas filtered
  6. washwashed with water
  7. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-0765d842534943d4b4ec74ac697b09aa
Source dataset
uspto-grants-2014_02
Patent number
US08642607B2

Linked notes

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