Sodium Hydroxide → (5-Benzyloxybiphenyl-3-yl)acetic acid

HRID 1169944Notes

Reaction equation

HRID 1169944 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:28])[CH2:7][C:8]1[CH:9]=[C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:11]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]=1)C>CCO.Cl>[CH2:15]([O:14][C:12]1[CH:13]=[C:8]([CH2:7][C:6]([OH:28])=[O:5])[CH:9]=[C:10]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:11]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66702489(5-Benzyloxy-biphenyl-3-yl)acetic acid ethyl ester

Product 1

HCID 11551463(5-Benzyloxybiphenyl-3-yl)acetic acidYield 90%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

NaOH solution (1 ml, 1M aq) was added to a solution of (5-benzyloxy-biphenyl-3-yl)acetic acid ethyl ester (0.12 g, 0.35 mmol) in EtOH (2 ml) and the mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with HCl solution (2M aq) and extracted with EtOAc (×3). The combined organic extracts were washed with water, brine, dried (MgSO4), filtered and concentrated under reduced pressure to give (5-benzyloxybiphenyl-3-yl)acetic acid (0.12 g, 0.31 mmol) as colourless solid in 90% yield. 1H NMR (CDCl3) δ 7.57-7.56 (m, 2H), 7.48-7.30 (m, 8H), 7.15-7.10 (m, 2H), 6.94-6.90 (m, 1H), 5.11 (s, 2H), 3.69 (s, 2H); LCMS method (A), RT=4.2 min.

Workup

  1. extractionextracted with EtOAc (×3)
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-676004ffd8b3440480566263b19d4ec4
Source dataset
uspto-grants-2010_11
Patent number
US07825160B2

Reaction notes

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