Lithium Hydroxide → 2-(4-(Tert-butoxycarbonyl)phenyl)acetic acid

HRID 1913770Notes

Reaction equation

HRID 1913770 reaction equation
C[O:2][C:3](=[O:18])[CH2:4][C:5]1[CH:17]=[CH:16][C:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:7][CH:6]=1.[OH-].[Li+]>O.C1COCC1>[C:12]([O:11][C:9]([C:8]1[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:18])=[O:2])=[CH:17][CH:16]=1)=[O:10])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57611856Tert-butyl 4-((methoxycarbonyl)methyl)benzoate

Product 1

HCID 598545182-(4-(Tert-butoxycarbonyl)phenyl)acetic acidYield 90.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.2 g (16.78 mmol) of tert-butyl 4-(2-methoxy-2-oxoethyl)benzoate in 50 ml of water and 50 ml of THF is mixed with 0.8 g (33.6 mmol) of lithium hydroxide and stirred at room temperature for 1 hour. The phases are separated and the aqueous phase is adjusted to pH 3 with 2 M hydrochloric acid. It is extracted with ethyl acetate. The organic phase is then washed with sodium chloride solution, dried over sodium sulphate and evaporated. 3.6 g (15.2 mmol, 87% yield) of the title compound are obtained.

Workup

  1. customThe phases are separated
  2. extractionIt is extracted with ethyl acetate
  3. washThe organic phase is then washed with sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-82a26dd3524d423295cd878441a65f93
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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