Dimethylformamide → Methyl (4-Hydroxybenzoyl)acetate

HRID 922241Notes

Reaction equation

HRID 922241 reaction equation
[H-].[Na+].CN(C=O)C.[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=1.[CH3:18][O:19][C:20](=O)[O:21]C>O>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH2:16][C:20]([O:19][CH3:18])=[O:21])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 74694'-HydroxyacetophenoneHCID 12021Dimethyl CarbonateHCID 24758Sodium hydride

Product 1

HCID 508465Methyl (4-Hydroxybenzoyl)acetateYield 48.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 250 mL RB flask fitted with magnetic stirrer was charged with sodium hydride (3.5 g, 147 mmol). At 0 deg C., 100 mL of DMF was added slowly with stirring. To the stirred solvent were added 1-(4-hydroxyphenyl)ethanone (5 g, 36 mmol) and dimethylcarbonate (15.5 g, 170 mmol), stirred at room temperature overnight. The RM was poured into water (100 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with water (50 mL) and saturated brine solution (50 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude material was purified by silica gel column chromatography using ethyl acetate and petroleum ether as elutants. The product was obtained as pale yellow oil (3.4 g, yield: 47.66%). MS (ESI, 120 eV): m/z=195 (M+H)+; 1H NMR (300 MHz, CDCl3): δ 7.79-7.82 (d, 2H), 6.81-6.84 (d, 2H), 6.21 (br s, 1H), 3.90 (s, 2H), 3.69 (s, 3H).

Workup

  1. customTo a 250 mL RB flask fitted with magnetic stirrer
  2. customAt 0 deg C
  3. stirringstirred at room temperature overnight
  4. extractionextracted with ethyl acetate (100 mL)
  5. washThe organic layer was washed with water (50 mL) and saturated brine solution (50 mL)
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. customthe solvent was removed under reduced pressure
  8. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5f3f289b03044a8e9bdf3a2cbe6387f6
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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