Water → Methyl 2,3,4-trimethoxybenzoate

HRID 456029

Reaction equation

HRID 456029 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 it 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. additionwas added
  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-3216ad2980eb4cd08a2d71088f0d0ca0
Source dataset
uspto-grants-2013_07
Patent number
US08497380B2

Linked notes

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