Ethylparaben → Ethyl 4-hydroxy-3-(2-methylprop-2-en-1-yl)benzoate

HRID 1292094Notes

Reaction equation

HRID 1292094 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.[CH2:13](Cl)[C:14](=[CH2:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][C:12]=1[CH2:15][C:14](=[CH2:13])[CH3:16]

Participants

5

Reactant 3

HCID 8434EthylparabenHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium Carbonate

Product 1

HCID 18705333Ethyl 4-hydroxy-3-(2-methylprop-2-en-1-yl)benzoateYield 89.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 4-hydroxybenzoate (50.0 g), methallyl chloride (32.6 g), and potassium carbonate (45.6 g) were refluxed in acetone (150 ml) with stirring for 40 hours. The reaction mixture was filtered and the filtrate was concentrated under a vacuum. The residue, with toluene (150 ml) added thereto, was washed with 2% sodium hydroxide solution and water successively. After being dried over sodium sulfate anhydride, the solution was concentrated under a vacuum. The resulting oily material was dissolved in N,N-dimethylaniline (80 ml) and refluxed with stirring for about 10 hours. The reaction mixture was acidified with concentrated hydrochloric acid while being cooled with ice and then extracted with toluene. The extract was further extracted with 10% aqueous sodium hydroxide solution. The resulting water layer was acidified with concentrated hydrochloric acid and then extracted with toluene. The extract was washed with water, dried over sodium sulfate anhydride, and then concentrated under a vacuum, thereby yielding 59.2 g of the aimed compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under a vacuum
  3. additionThe residue, with toluene (150 ml) added
  4. washwas washed with 2% sodium hydroxide solution and water successively
  5. dry with materialAfter being dried over sodium sulfate anhydride
  6. concentrationthe solution was concentrated under a vacuum
  7. dissolutionThe resulting oily material was dissolved in N,N-dimethylaniline (80 ml)
  8. temperaturerefluxed
  9. stirringwith stirring for about 10 hours
  10. temperaturewhile being cooled with ice
  11. extractionextracted with toluene
  12. extractionThe extract was further extracted with 10% aqueous sodium hydroxide solution
  13. extractionextracted with toluene
  14. washThe extract was washed with water
  15. dry with materialdried over sodium sulfate anhydride
  16. concentrationconcentrated under a vacuum

Sources & evidence

ORD record
ord-58e6ada6ce104b4cbbe27938588984b7
Source dataset
uspto-grants-1998_05
Patent number
US05756505

Reaction notes

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