Water → 3-Biphenylylacetic acid

HRID 719592

Reaction equation

HRID 719592 reaction equation
O.O.[OH-].[Li+].C[O:6][C:7](=[O:21])[CH2:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1>CO>[C:11]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=[C:9]([CH2:8][C:7]([OH:21])=[O:6])[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 10751722Biphenyl-3-ylacetic acid methyl ester

Product 1

HCID 321533-Biphenylylacetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Water (39 mL), followed by lithium hydroxide monohydrate (4.2 g, 101.5 mmol) were added to a solution of biphenyl-3-yl acetic acid methyl ester (11.43 g, 50.57 mmol) in methanol (265 mL). The mixture was stirred at ambient temperature for 2h then the organics were removed under reduced pressure. The mixture was acidified with dilute hydrochloric acid (1M, 80 mL), extracted with chloroform (2×100 mL), dried (MgSO4) and evaporated under reduced pressure to afford biphenyl-3-yl acetic acid as a white solid, yield 10.6 g, (99%), analytical HPLC Rt=16.565 min, HPLC-MS (single main UV peak with Rt=7.91 min, 213.1 [M+H]+).

Workup

  1. customthe organics were removed under reduced pressure
  2. extractionextracted with chloroform (2×100 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5cbd748ebe3442bda3eabd2bd33eea59
Source dataset
uspto-grants-2006_11
Patent number
US07132449B2

Linked notes

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