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

HRID 22247

Reaction equation

HRID 22247 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-db788f0e684c4545913753d0f555e1f7
Source dataset
uspto-grants-1995_06
Patent number
US05428037

Linked notes

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