Lithium hydroxide, monohydrate → 2-(2,6-Dimethylphenyl)acetic acid

HRID 474300Notes

Reaction equation

HRID 474300 reaction equation
C([O:3][C:4](=[O:14])[CH2:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])C.O.[OH-].[Li+]>C1COCC1.O>[CH3:12][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:13])[C:6]=1[CH2:5][C:4]([OH:14])=[O:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 54752301Ethyl 2-(2,6-dimethylphenyl)acetate

Product 1

HCID 198401152-(2,6-Dimethylphenyl)acetic acidYield 78.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (2,6-dimethyl-phenyl)-acetic acid ethyl ester (13.3 g, 69.2 mmol) in THF (550 mL) and water (224 mL) was added lithium hydroxide monohydrate (23.2 g, 553 mmol). The resulting mixture was stirred vigorously at rt. After 72 h, the mixture was heated to 50° C. for an additional 24 h. The mixture was cooled to rt and concentrated. To the resulting residue was added aqueous 2 N HCl (300 mL) to afford a colorless precipitate. The precipitate was collected by vacuum filtration and further purified by FCC to provide a colorless solid (8.9 g, 78%). MS (ESI): mass calcd. for C10H12O2, 164.1; m/z found, 163.1 [M−H]+. 1H NMR (CDCl3): 7.17-6.90 (m, 3H), 3.72 (s, 2H), 2.33 (s, 6H).

Workup

  1. temperaturethe mixture was heated to 50° C. for an additional 24 h
  2. temperatureThe mixture was cooled to rt
  3. concentrationconcentrated
  4. additionTo the resulting residue was added aqueous 2 N HCl (300 mL)
  5. customto afford a colorless precipitate
  6. filtrationThe precipitate was collected by vacuum filtration
  7. customfurther purified by FCC

Sources & evidence

ORD record
ord-43898110e75b4e3480252e3d9756c608
Source dataset
uspto-grants-2014_01
Patent number
US08637527B2

Reaction notes

Loading…