Ethanol → 4-(4-Methoxybenzyl)benzoic acid

HRID 262196

Reaction equation

HRID 262196 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[OH-].[Na+].C(O)C>O>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][C:8]2[CH:18]=[CH:17][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 12463843Ethyl 4-(4-methoxybenzyl)benzoate

Product 1

HCID 2579874-(4-Methoxybenzyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 120 g. of ethyl 4-(4-methoxybenzyl)benzoate, 500 ml. of 2N sodium hydroxide solution and 250 ml. of ethanol was heated at reflux for two hours. The reaction mixture was cooled, diluted with water and extracted with ether. The aqueous layer was acidified with hydrochloric acid and the precipitate which formed was collected and dried to give 100 g. of 4-(4-methoxybenzyl)benzoic acid, m.p. 152°-153° C. when recrystallized from aqueous ethanol.

Workup

  1. additionA mixture of 120 g
  2. temperatureat reflux for two hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ether
  5. customthe precipitate which formed
  6. customwas collected
  7. customdried
  8. customto give 100 g
  9. customof 4-(4-methoxybenzyl)benzoic acid, m.p. 152°-153° C. when recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-889d59a7cbbb4fa697ab2726d32b1588
Source dataset
uspto-grants-1979_05
Patent number
US04153719

Linked notes

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