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

HRID 1613894Notes

Reaction equation

HRID 1613894 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-bbae589110c14671b4521e63a187a77a
Source dataset
uspto-grants-1993_03
Patent number
US05194588

Reaction notes

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