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

HRID 1354019Notes

Reaction equation

HRID 1354019 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-42db4511a15b45eea33ce563c3f4e504
Source dataset
uspto-grants-2007_05
Patent number
US07223752B2

Reaction notes

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