2,6-Dimethoxybenzoic Acid → Benzoic acid, 2,6-dimethoxy-, methyl ester

HRID 1058174

Reaction equation

HRID 1058174 reaction equation
N12CCCN=C1CCCC[CH2:2]2.[CH3:12][O:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:15]=1[C:16]([OH:18])=[O:17]>C(=O)(OC)OC.CCOC(C)=O.O>[CH3:24][O:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:14]([O:13][CH3:12])[C:15]=1[C:16]([O:18][CH3:2])=[O:17]

Participants

6

Reactant 2

HCID 151092,6-Dimethoxybenzoic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 137419Benzoic acid, 2,6-dimethoxy-, methyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 12021Dimethyl CarbonateSolvent

Conditions

Temperature
90 °C

Procedure

1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), (836 mg, 5.49 mmol), was added to a mixture of 2,6-dimethoxybenzoic acid (1), (1.0 g, 5.49 mmol), in dimethyl carbonate (DMC) (10 mL) and the resulting mixture was heated to reflux at 90° C. for 4 hours. The reaction mixture was cooled to 25° C. and diluted with EtOAc (30 mL) and water (30 mL). The organic layer was separated and washed in sequence with 10 mL of water, 2 M HCl (2×30 mL), saturated aqueous NaHCO3 (2×30 mL) and water (2×25 mL). The organic layer was dried over Na2SO4, filtered and concentrated under vacuum to give methyl 2,6-dimethoxybenzoate (2) as a white solid. The yield of the 2,6-dimethoxybenzoate as determined by HPLC was 97-98% conversion.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureThe reaction mixture was cooled to 25° C.
  3. customThe organic layer was separated
  4. washwashed in sequence with 10 mL of water, 2 M HCl (2×30 mL), saturated aqueous NaHCO3 (2×30 mL) and water (2×25 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-107e392ba5f74beaa591bfe07c008edd
Source dataset
uspto-grants-2003_02
Patent number
US06515167B1

Linked notes

Loading…