Methanol → HCID 22934046, compound

HRID 1269867Notes

Reaction equation

HRID 1269867 reaction equation
CO.[CH3:3][C:4]1[CH:13]=[C:12]([C:14]([O:16]C)=[O:15])[C:11]([CH3:18])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7].[OH-].[Li+]>O1CCCC1>[CH3:9][O:8][C:6]([C:5]1[C:4]([CH3:3])=[CH:13][C:12]([C:14]([OH:16])=[O:15])=[C:11]([CH3:18])[CH:10]=1)=[O:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 289462Dimethyl 2,5-dimethylbenzene-1,4-dicarboxylate

Product 1

HCID 22934046HCID 22934046, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanol (20 ml) was added to a solution of dimethyl 2,5-dimethylterephthalate (3.95 g, 17.8 mmol) in tetrahydrofuran (40 ml) and the resulting mixture was cooled on a water bath. A 2N-aqueous lithium hydroxide solution (9.8 ml, 19.6 mmol) was slowly added thereto and stirred for 3 hours. The solvent was distilled off under reduced pressure and the residue was adjusted to pH 1 to 2 with a 1N-hydrochloric acid and extracted with ethyl acetate (×3). The extract solution was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by a silica gel chromatography (eluent: chloroform/methanol=30/1) to obtain 4-(methoxycarbonyl)-2,5-dimethylbenzoic acid (2.77 g, 75%).

Workup

  1. temperaturethe resulting mixture was cooled on a water bath
  2. distillationThe solvent was distilled off under reduced pressure
  3. extractionextracted with ethyl acetate (×3)
  4. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by a silica gel chromatography (eluent: chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-808cc1f1271e4e828c497c71330b4a77
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

Loading…