Ethylparaben → Ethyl 4-[2-Oxo-2-(phenylmethoxy)ethoxy]benzoate

HRID 1165528Notes

Reaction equation

HRID 1165528 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.Br[CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[O:16]=[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:14][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetate

Product 1

HCID 53990693Ethyl 4-[2-Oxo-2-(phenylmethoxy)ethoxy]benzoateYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl p-hydroxybenzoate (4.98 g), benzyl bromoacetate (4.75 ml) and K2CO3 (4.14 g) was stirred for 15 hr in 30 ml of DMF. The reaction mixture was diluted with water (200 ml) and extracted with a 1:1 ether:hexane mixture. The combined organic extracts were washed (water, brine), dried (Na2SO4), filtered, and evaporated leaving 9.3 g, (99%) of the title compound as a heavy oil; TLC, Rf =0.71, Et2O: hexane (1:1).

Workup

  1. extractionextracted with a 1:1 ether
  2. washThe combined organic extracts were washed (water, brine)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-69925cfc04844c2799a5ef36da732046
Source dataset
uspto-grants-1990_03
Patent number
US04910190

Reaction notes

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