Hydrochloric Acid → 4-Benzyloxyphenylacetic acid

HRID 433825Notes

Reaction equation

HRID 433825 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) δ3.63 (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-fa981f3f0214461499b4d5dd9b9028d9
Source dataset
uspto-grants-2003_12
Patent number
US06668527B2

Reaction notes

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