Sodium Hydroxide → 2'-Methoxy-biphenyl-4-carboxylic acid

HRID 1070416Notes

Reaction equation

HRID 1070416 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]=[CH:14][C:13]=2[O:18][CH3:19])=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Na+]>O1CCCC1>[CH3:19][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:9]1[CH:10]=[CH:11][C:6]([C:4]([OH:5])=[O:3])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 438402982'-Methoxy-biphenyl-4-carboxylic acid ethyl ester

Product 1

HCID 27595482'-Methoxy-biphenyl-4-carboxylic acidYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2′-methoxy-[1,1′-biphenyl]-4-carboxylic acid ethyl ester of Step A (3.7 g, 14.4 mmol) in tetrahydrofuran (40 mL) and 1 N sodium hydroxide (30 mL, 30 mmol) was heated at reflux overnight. After cooling, the reaction mixture was concentrated in vacuo, and the residue was acidified with 2N hydrochloric acid to give a white solid which was collected by filtration and dried under vacuum to provide the title compound (3.2 g, 97.4%) as a white solid, m.p. 250-253° C.

Workup

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

Sources & evidence

ORD record
ord-f55b762bdda741a69d85a3996b200959
Source dataset
uspto-grants-2005_06
Patent number
US06903091B2

Reaction notes

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