Water → HCID 12398522, compound

HRID 866370Notes

Reaction equation

HRID 866370 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.O>[O-]CC.[Na+]>[CH2:9]([O:8][C:6]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([Cl:13])=[CH:15][CH:16]=2)=[CH:12][CH:11]=1)=[O:7])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 8434Ethylparaben

Product 1

HCID 12398522HCID 12398522, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

To a solution of ethyl 4-hydroxybenzoate (8.3g.) in sodium ethoxide solution (1.15g. sodium in 70 ml. of absolute ethanol) was added p-chlorobenzylchloride (8.1g.) in one portion. The mixture was heated under reflux for 16 hours, allowed to cool and poured into water (500 mls.) and the product extracted into ether. The organic layer was separated and dried (anhydrous MgSO4) and filtered. Evaporation of the solvent under reduced pressure gave the crude product which on recrystallation from ethanol, yielded by 4-ethoxycarbonylphenoxy-4-chlorophenyl methane (8.5g.), m.pt. 83°-84° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. temperatureto cool
  4. extractionthe product extracted into ether
  5. customThe organic layer was separated
  6. dry with materialdried (anhydrous MgSO4)
  7. filtrationfiltered
  8. customEvaporation of the solvent under reduced pressure
  9. customgave the crude product which on recrystallation from ethanol

Sources & evidence

ORD record
ord-574ba62ef1c84fc98ab33d514ac14402
Source dataset
uspto-grants-1978_07
Patent number
US04098816

Reaction notes

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