Methyl anisate → Methyl anisate

HRID 1006310Notes

Reaction equation

HRID 1006310 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18](C=O)=[CH:17][CH:16]=1.[OH:23]OS([O-])=O.[K+].CCOC(C)=O>CO>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([OH:23])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 8499Methyl anisateHCID 8857Ethyl AcetateHCID 312444-MethoxybenzaldehydeHCID 23707502Potassium hydroxy sulfite

Product 2

HCID 8499Methyl anisateHCID 90154-Methoxyphenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To prepare methyl 4-methoxybenzoate, 4-methoxybenzaldehyde (100 mg) was dissolved in MeOH (10 mL), and OXONE (0.451 g) was added and stirred at room temperature for 18 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 methyl 4-methoxybenzoate in 19% yield and 4-methoxy phenol in 77% yield after purification by silica gel column chromatography.

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-7a16d75965a9441eaff707f4c4c6f41c
Source dataset
uspto-grants-2004_09
Patent number
US06787671B2

Reaction notes

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