Ethanol → Ethyl 4-(phenylmethoxy)benzoate

HRID 866371Notes

Reaction equation

HRID 866371 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1.[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)C>CN(C)C=O.O>[CH2:11]([O:10][C:8]([C:7]1[CH:6]=[CH:5][C:4]([O:3][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][CH:13]=1)=[O:9])[CH3:12]

Participants

7

Reactant 4

HCID 702EthanolHCID 7503Benzyl ChlorideHCID 8434EthylparabenHCID 24758Sodium hydride

Product 1

HCID 191414Ethyl 4-(phenylmethoxy)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (4.8g. of 50% suspension in oil) was added to a solution of ethyl p-hydroxybenzoate (166g.) in dimethylformamide (1 l). Benzyl chloride (126 g.) was added dropwise to the solution and the mixture heated on a steam bath for 2 hours. The solution was allowed to cool and ethanol (100 mls.) was added and the mixture poured into water (3 l) and then extracted with chloroform. The organic layer was dried (anhydrous MgSO4), filtered and the solvent removed under high vacuum. The resulting crude product was recrystallized from ethanol to yield pure 4-ethoxycarbonylphenoxyphenyl methane (154.2g.), b.pt. 172-3 at 10mm Hg.

Workup

  1. temperaturethe mixture heated on a steam bath for 2 hours
  2. temperatureto cool
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried (anhydrous MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed under high vacuum
  7. customThe resulting crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-728d540e986f46c289eb5323226bdb50
Source dataset
uspto-grants-1978_07
Patent number
US04098816

Reaction notes

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