Hydrochloric Acid → 4-Benzyloxyphenylacetic acid

HRID 1071280Notes

Reaction equation

HRID 1071280 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.[OH-].[Li+].Cl>CO.O1CCCC1>[CH2:12]([O:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:19])=[O:2])=[CH:10][CH:9]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 2756645Methyl 2-(4-benzyloxyphenyl)acetate

Product 1

HCID 810334-Benzyloxyphenylacetic acidYield 98%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 1:2 methanol/tetrahydrofuran (60 mL) solution of (4-benzyloxy-phenyl)-acetic acid methyl ester (1.35 g, 5.27 mmol) was combined with 2M aqueous lithium hydroxide (20 mL) at room temperature and the reaction was stirred overnight. The reaction was acidified to pH 1 with 1N hydrochloric acid and extracted with ethyl acetate (2×50 mL). The organic portions were dried over sodium sulfate and the solvent removed in vacuo to give the title compound as a white crystalline solid (1.25 g, 98%). 1H NMR (300 MHz, CDCl3) δ 3.63 (s, 2H), 5.09 (s, 2H), 6.96-6.99 (d, 2H), 7.22-7.25 (d, 2H), 7.3-7.5 (m, 5H).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. dry with materialThe organic portions were dried over sodium sulfate
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-1b0f495cf7d14d6facbe9bfa964e0179
Source dataset
uspto-grants-2005_06
Patent number
US06903128B2

Reaction notes

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