Sodium Hydroxide → 4'-Methoxy(1,1'-biphenyl)-4-carboxylic acid

HRID 2375153Notes

Reaction equation

HRID 2375153 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Na+]>O1CCCC1>[CH3:19][O:18][C:15]1[CH:14]=[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]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2764348Ethyl 4'-methoxy[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 27595524'-Methoxy(1,1'-biphenyl)-4-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the ester of Step A (3.9 g, 15.2 mmol) in tetrahydrofuran (50 mL) was treated with 1 N sodium hydroxide (31 mL, 31 mmol) and then heated at reflux overnight. After cooling, the reaction mixture was concentrated in vacuo. 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 (3.4 g, 98.0%) as a white solid, m.p. 250-254° C.

Workup

  1. temperatureheated
  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-4246e0c7a0f54ec4be4ab162b289745c
Source dataset
uspto-grants-2008_12
Patent number
US07465722B2

Reaction notes

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