Sodium Hydroxide → 4'-Methyl-biphenyl-3-carboxylic acid

HRID 1077829

Reaction equation

HRID 1077829 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16]CC)=[O:15])[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:16])=[O:15])[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 107287544'-Methyl-biphenyl-3-carboxylic acid ethyl ester

Product 1

HCID 27739784'-Methyl-biphenyl-3-carboxylic acidYield 67.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4'-methylbiphenyl-3-carboxylate (4.0 g) in ethanol (50 ml) was added a solution of 10 ml of 10% aqueous sodium hydroxide, and the mixture refluxed for 2 hours. Solvent was removed under reduced pressure, water added to the residue, and the solution filtered. The filtrate was acidified with dilute hydrochloric acid, and the white solid filtered off and dried under vacuum, yielding 2.4 g of 4'-methylbiphenyl-3-carboxylic acid m.p. 192° C.

Workup

  1. temperaturethe mixture refluxed for 2 hours
  2. customSolvent was removed under reduced pressure, water
  3. additionadded to the residue
  4. filtrationthe solution filtered
  5. filtrationthe white solid filtered off
  6. customdried under vacuum

Sources & evidence

ORD record
ord-caafe567a20a4754856bf9f188721866
Source dataset
uspto-grants-1996_08
Patent number
US05545645

Linked notes

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