Methyl iodide → Methyl 4-propanoylbenzoate

HRID 606594Notes

Reaction equation

HRID 606594 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].[C:14]([O-])(O)=O.[Na+].IC>CN(C=O)C.[Na+].[Cl-]>[CH3:14][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:5]([C:1](=[O:4])[CH2:2][CH3:3])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 20202p-Propionylbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 15666905Methyl 4-propanoylbenzoateYield 77.4%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent

Procedure

4-propionylbenzoic acid (890 mg, 5 mmol), NaHCO3 (1.26 g, 15 mmol), and iodomethane (935 μL, 15 mmol) in DMF (10 mL) were stirred at RT overnight. The mixture was diluted with saturated aqueous NaCl (50 mL) and extracted with ether (3×50 mL). The organic phase was washed with water (50 mL), dried, and evaporated. Flash chromatography (90 g silica, 2/1 petroleum ether—EtOAc) gave white solids of 4-Propionyl-benzoic acid methyl ester (744 mg, 77%).

Workup

  1. extractionextracted with ether (3×50 mL)
  2. washThe organic phase was washed with water (50 mL)
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-1d84fb9e4c3745f0a814f70e41eec3d0
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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