Ethylparaben → HCID 19983177, compound

HRID 1460205Notes

Reaction equation

HRID 1460205 reaction equation
Br[CH2:2][CH2:3][CH:4]=[CH2:5].[OH:6][C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)C>[CH2:2]([O:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:16][CH:17]=1)[CH2:3][CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 21241Homoallyl bromide

Product 1

HCID 19983177HCID 19983177, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 50 parts of 4-bromo-1-butene, 58 parts of ethyl 4-hydroxybenzoate, 55.2 parts of potassium carbonate and 320 parts of 2-propanone was refluxed for 68 hours. The reaction mixture was evaporated and the residue was dissolved in methylbenzene. The organic solution was washed with a diluted sodium hydroxide solution. The separated organic layer was dried, filtered and evaporated, yielding 25 parts (33%) of ethyl 4-(3-butenyloxy)benzoate as an oily residue (interm. 14).

Workup

  1. temperaturewas refluxed for 68 hours
  2. customThe reaction mixture was evaporated
  3. dissolutionthe residue was dissolved in methylbenzene
  4. washThe organic solution was washed with a diluted sodium hydroxide solution
  5. customThe separated organic layer was dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a0aba6fa44274523b7c3bc5f2b75ded0
Source dataset
uspto-grants-1991_12
Patent number
US05070090

Reaction notes

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