Formic Acid → Methyl 4-formyl-2-methylbenzoate

HRID 1501163Notes

Reaction equation

HRID 1501163 reaction equation
C(C1[CH:11]=[CH:10][C:6]([C:7]([O-:9])=[O:8])=[C:5]([CH3:12])[CH:4]=1)#N.[CH:13](O)=O.[CH2:16]([OH:18])[CH3:17]>[Ni]>[CH:16]([C:17]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:13])=[O:8])=[C:5]([CH3:12])[CH:4]=1)=[O:18]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 702EthanolHCID 86314816HCID 86314816, compound

Product 1

HCID 20134203Methyl 4-formyl-2-methylbenzoateYield 65%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Conditions

Temperature
110 °C

Procedure

Raney-Ni (3.0 mL, washed with ethanol for 3 times) was added to a solution of 4-cyano-2-methylbenzoate (0.93 g, 5.3 mmol) in ethanol (20 mL). Then formic acid (10 mL, 75%) was added to the mixture. The mixture was stirred at 110° C. for 2 hours. After filtration, the mixture was concentrated. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1) to gave product methyl 4-formyl-2-methylbenzoate as a yellow oil (620 mg, 65%).

Workup

  1. filtrationAfter filtration
  2. concentrationthe mixture was concentrated
  3. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1)

Sources & evidence

ORD record
ord-7095896be6f943ec99944b63ca60e23d
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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