Sodium hydride → Methyl [4-(4-methoxybenzoyl)-2-methylphenoxy]acetate

HRID 1649956Notes

Reaction equation

HRID 1649956 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[O:7])=[CH:4][C:3]=1[CH3:18].[H-].[Na+].Br[CH2:22][C:23]([O:25][CH3:26])=[O:24]>CN(C=O)C>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:5]2[CH:16]=[CH:17][C:2]([O:1][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[C:3]([CH3:18])[CH:4]=2)=[O:7])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 13966818HCID 13966818, compound

Product 1

HCID 13966816Methyl [4-(4-methoxybenzoyl)-2-methylphenoxy]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 g of 4-hydroxy-3-methyl-4'-methoxybenzophenone (R. Martin et al. Monatsh. Chemie 110, 1057-1066 (1979)) are dissolved in 200 ml of dry DMF and, under N2, 9 g of a 55% dispersion of sodium hydride in mineral oil are cautiously added. Then, while stirring, 19.5 ml of methyl bromoacetate are added dropwise, and the mixture is left to stand at room temperature overnight. The precipitated salt is filtered off with suction, and the filtrate is concentrated in vacuo. The residue is taken up in ethyl acetate, and the solution is washed with sodium bicarbonate solution and water. The organic phase is dried over magnesium sulfate, and the solvent is removed in vacuo. The residue is triturated with ether, filtered off with suction and dried.

Workup

  1. waitthe mixture is left
  2. filtrationThe precipitated salt is filtered off with suction
  3. concentrationthe filtrate is concentrated in vacuo
  4. washthe solution is washed with sodium bicarbonate solution and water
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customthe solvent is removed in vacuo
  7. customThe residue is triturated with ether
  8. filtrationfiltered off with suction
  9. customdried

Sources & evidence

ORD record
ord-b62a71e5efb74246af51a330d376a20e
Source dataset
uspto-grants-1990_05
Patent number
US04922015

Reaction notes

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