4-Methoxybenzoic Acid → 4-Methoxybenzoic Acid

HRID 1006312Notes

Reaction equation

HRID 1006312 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17](C=O)=[CH:16][CH:15]=1.OOS([O-])=O.[K+].CC[O:30][C:31](C)=[O:32]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[CH:31]([O:32][C:17]1[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[CH:21][CH:20]=1)=[O:30]

Participants

7

Reactant 4

HCID 74784-Methoxybenzoic AcidHCID 8857Ethyl AcetateHCID 312444-MethoxybenzaldehydeHCID 23707502Potassium hydroxy sulfite

Product 2

HCID 74784-Methoxybenzoic AcidHCID 10171253HCID 10171253, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To prepare 4-methoxybenzoic acid, 4-methoxybenzaldehyde (100 mg) was dissolved in DMF (10 mL), and OXONE (0.451 g) was added and stirred at room temperature for 3 hours with the reaction having a final volume (11 mL). The reaction was monitored by TLC or GC analysis. EtOAc was added to extract the products and 1N HCl was used to dissolve the salts. The organic extract was washed with 1N HCl (30 mL×3) and brine (30 mL), dried over Na2SO4, and the solvent was removed under reduced pressure to obtain 4-methoxybenzoic acid in 31% yield and 4-methoxyphenol formate in 58% yield after purification by silica gel column chromatography. 4-Methoxyphenyl Formate: 1H NMR (CDCl3, 300 MHz): δ8.26 (s, 1H), 7.03 (d, 2H, J=9.0), 6.89 (d, 2H,J=8.9), 3.78 (s, 3H); 13C NMR (CDCl3, 75 MHz): 8176.7, 170.5, 79.9, 74.3, 31.4, 30.4, 28.2, 24.8, 23.9, 22.4, 20.9, 13.9.

Workup

  1. extractionto extract the products and 1N HCl
  2. dissolutionto dissolve the salts
  3. extractionThe organic extract
  4. washwas washed with 1N HCl (30 mL×3) and brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9bccc6f5a3574f6f87e4cbc9b012b47f
Source dataset
uspto-grants-2004_09
Patent number
US06787671B2

Reaction notes

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