Water → Methyl 2,3,4-trimethoxybenzoate

HRID 456029

Reaktionsgleichung

Reaktionsgleichung von HRID 456029
[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]

Komponenten

7

Edukt 4

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

Produkt 1

HCID 13940801Methyl 2,3,4-trimethoxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3216ad2980eb4cd08a2d71088f0d0ca0
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497380B2

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