Formic Acid → Methyl 3-methoxy-5-propylbenzoate
Reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][CH3:12])[C:7](OS(C(F)(F)F)(=O)=O)=[C:6]([O:21][CH3:22])[CH:5]=1.CN(C=O)C.CCN(CC)CC.C(O)=O>C([O-])(O)=O.[Na+].CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][CH3:12])[CH:7]=[C:6]([O:21][CH3:22])[CH:5]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 60 °C
Procedure
To a mixture of 3-methoxy-5-propyl-4-trifluoromethanesulfonyloxybenzoic acid methyl ester (1.0 g, 2.8 mmol), Pd(OAc)2 (31 mg, 0.138 mmol) and 1,1′-bis-(diphenylphosphino)ferrocene (155 mg, 0.28 mmol) at room temperature was added DMF (20 mL), then Et3N (1.17 mL, 8.4 mmol) followed by formic acid (0.21 mL, 5.6 mmol). The resulting mixture was stirred at 60° C. for 2 h and cooled to room temperature. The reaction mixture was diluted with aqueous NaHCO3 solution (150 mL) and then extracted with EtOAc (3×70 mL). The combined organic layer was washed with brine (100 mL), dried over Na2SO4, concentrated in vacuo, and the residue was purified by column chromatography to afford 3-methoxy-5-propylbenzoic acid methyl ester (0.56 g).
Workup
- temperaturecooled to room temperature
- extractionextracted with EtOAc (3×70 mL)
- washThe combined organic layer was washed with brine (100 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customthe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-05669f44e31648cf8489c6ca2f18d06e
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691843B2
Reaction notes
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