Water → Methyl 2,3,4-trimethoxybenzoate

HRID 1686085Notes

Reaction equation

HRID 1686085 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[C:16]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[CH:8][C:4]=1[C:5]([O:7][CH3:16])=[O:6]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 113082,3,4-Trimethoxybenzoic acidHCID 11430Potassium Carbonate

Product 1

HCID 13940801Methyl 2,3,4-trimethoxybenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

2,3,4-Trimethoxybenzoic acid (Aldrich) (20 g, 94 mmol) was dissolved in dry DMF (250 mL). K2CO3 (13 g, 94 mmol) and MeI (6.5 mL, 103.4 mmol) were added and the reaction mixture was heated to 50° C. for 5 h. The reaction mixture was cooled to rt and water (250 mL) was added. EtOAc (1 L) was added and the organic phase was washed with water (3×500 mL) and finally with NaCl (sat.). The organic phase washed dried over MgSO4, filtered and concentrated in vacuo. Redissolved in toluene and evaporated. Methyl 2,3,4-trimethoxybenzoate was obtained as a slightly yellow oil. 1H NMR (CDCl3) δ=7.60 (1H, d), 6.70 (1H, d), 3.99 (3H, s), 3.91 (3H, s), 3.89 (3H, s), 3.88 (3H, s). Yield 21 g (99%).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. washthe organic phase was washed with water (3×500 mL) and finally with NaCl (sat.)
  3. washThe organic phase washed
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionRedissolved in toluene
  8. customevaporated

Sources & evidence

ORD record
ord-f64a66f2df9c42448b36e8dfe1429527
Source dataset
uspto-grants-2012_04
Patent number
US08148537B2

Reaction notes

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