Water → Methyl 3-formyl-4-methoxybenzoate

HRID 419302Notes

Reaction equation

HRID 419302 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])=[O:2].[C:14]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C.C(OCC)C>[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 212595Benzoic acid, 3-formyl-4-hydroxy-, methyl ester

Product 1

HCID 15192109Methyl 3-formyl-4-methoxybenzoateYield 101.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl 3-formyl-4-hydroxybenzoate (2.06 g, 11.4 mmol) and K2CO3 (2.36 g, 17.1 mmol) were stirred in 50 mL of DMF. Methyl iodide (1.42 mL, 22.8 mmol) was added via syringe, and the reaction was stirred for 6 hours at rt. The reaction was poured into H2O and diethyl ether, and the layers were separated. The organic layer was washed with brine, and the combined aqueous layers were extracted with diethyl ether. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to afford 2.24 g of crude desired product. 1H NMR (400 MHz, DMSO-d6): δ 10.33 (s, 1H), 8.23 (d, J=2.2 Hz, 1H), 8.20 (dd, J=8.8, 2.2 Hz, 1H), 7.36 (d, J=8.8 Hz, 1H), 3.99 (s, 3H), 3.83 (s, 3H).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. extractionthe combined aqueous layers were extracted with diethyl ether
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a9459630ed0c4d18a2a5709ebf778c0d
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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