Lithium Hydroxide → 2-(4-(Methoxycarbonyl)phenyl)acetic acid

HRID 1257473Notes

Reaction equation

HRID 1257473 reaction equation
C[O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1.[OH-].[Li+]>O1CCCC1.O>[CH3:12][O:11][C:9]([C:8]1[CH:13]=[CH:14][C:5]([CH2:4][C:3]([OH:15])=[O:2])=[CH:6][CH:7]=1)=[O:10]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 10536335Benzeneacetic acid, 4-(methoxycarbonyl)-, methyl ester

Product 1

HCID 107978792-(4-(Methoxycarbonyl)phenyl)acetic acidYield 102.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-(2-methoxy-2-oxoethyl)benzoate (13.6 g) was dissolved in tetrahydrofuran (180 mL) and water (60 mL), and lithium hydroxide (2.75 g) was added. The reaction mixture was heated at room temperature for 24 hr, stirred and concentrated under reduced pressure. The residue was diluted with water, and washed with ethyl acetate. The aqueous layer was adjusted with 2.5N hydrochloric acid to pH 5-6, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure to give the title compound (13.0 g) as a colorless solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. washwashed with ethyl acetate
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f15fd899831a492785e698d7bfcae238
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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