Sodium Hydroxide → 4-(3-Methylphenyl)benzoic acid

HRID 1354016Notes

Reaction equation

HRID 1354016 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=2)=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Na+]>O1CCCC1>[CH3:18][C:14]1[CH:13]=[C:12]([C:9]2[CH:10]=[CH:11][C:6]([C:4]([OH:5])=[O:3])=[CH:7][CH:8]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 208200733'-Methyl-biphenyl-4-carboxylic acid ethyl ester

Product 1

HCID 27598164-(3-Methylphenyl)benzoic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3′-methyl-[1.1′-biphenyl]-4-carboxylic acid ethyl ester of Step A (3.3 g, 13.7 mmol) in tetrahydrofuran (40 mL) and 1 N sodium hydroxide (27.5 mL, 27.5 mmol) was heated at reflux overnight. After cooling, the reaction was concentrated in vacuo. The residue was acidified with 2N hydrochloric acid to yield a white solid which was collected by filtration and dried under vacuum to provide the title compound (2.9 g, 99.7%) as a white solid, m.p. 198–200° C.

Workup

  1. temperatureat reflux overnight
  2. temperatureAfter cooling
  3. concentrationthe reaction was concentrated in vacuo
  4. customto yield a white solid which
  5. filtrationwas collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-ff1c452f9efe4f1197c69977a9f38e9c
Source dataset
uspto-grants-2007_05
Patent number
US07223752B2

Reaction notes

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