Methanol → Methyl 3-[dimethoxy(phenyl)methyl]benzoate

HRID 2184328Notes

Reaction equation

HRID 2184328 reaction equation
[CH3:1][OH:2].[C:3]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14](O)=[O:15])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:20]S(O)(=O)=O.[CH:25](OC)(OC)[O:26]C>C(OCC)(=O)C>[CH3:1][O:2][C:14](=[O:15])[C:13]1[CH:17]=[CH:18][CH:19]=[C:11]([C:3]([O:10][CH3:20])([O:26][CH3:25])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6395Methanesulfonic AcidHCID 9005Trimethyl orthoformateHCID 1013863-Benzoylbenzoic acid

Product 1

HCID 20792924Methyl 3-[dimethoxy(phenyl)methyl]benzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A methanol solution (15 mL) of 3-benzoyl-benzoic acid (2 g, 8.84 mmol) and methanesulfonic acid (0.115 mL, 1.77 mmol) was heated at 65° C. for 20 h and then cooled to room temperature. To this solution was added trimethyl orthoformate (1.45 mL, 13.26 mmol) and stirring continued for 24 h. The reaction solution was then diluted with ethyl acetate and washed with NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated. Flash chromatography (20 hexanes: 1 ethyl acetate +0.25% triethyl amine) provided 3-(dimethoxy-phenyl-methyl)-benzoic acid methyl ester (951 mg) as an oil.

Workup

  1. washwashed with NaHCO3
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-47fc4ab5ab3e4bd6afad55ee64cdbfad
Source dataset
uspto-grants-2005_05
Patent number
US06900336B2

Reaction notes

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