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

HRID 2287470Notes

Reaction equation

HRID 2287470 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+].Cl>CC(C)=O.CN(C)C1C=CC=CC=1>[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 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 2

HCID 180AcetoneSolventHCID 949N,N-DimethylanilineSolvent

Procedure

Ethyl 4-hydroxybenzoate (50.0 g), methallyl chloride (32.6 g) and potassium carbonate (45.6 g) were refluxed with heating in acetone (150 ml) for 40 hours. The reaction mixture was filtrated and the filtrate was concentrated under a vacuum. The residue, after toluene (150 ml) was added thereto, was washed with 2% sodium hydroxide aqueous solution and water successively. The extract was dried over sodium sulfate anhydride and then concentrated under a vacuum, thereby yielding an oily compound. This compound was dissolved in N,N-dimethylaniline (80 ml) and refluxed with heating for about 10 hours. While being cooled with ice, the reaction mixture was acidified with concentrated hydrochloric acid and then extracted with toluene. The extract was extracted with 10% sodium hydroxide aqueous solution. The 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 ethyl 4-hydroxy-3-methallylbenzoate.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. concentrationthe filtrate was concentrated under a vacuum
  3. additionThe residue, after toluene (150 ml) was added
  4. washwas washed with 2% sodium hydroxide aqueous solution and water successively
  5. dry with materialThe extract was dried over sodium sulfate anhydride
  6. concentrationconcentrated under a vacuum
  7. customyielding an oily compound
  8. temperaturerefluxed
  9. temperaturewith heating for about 10 hours
  10. temperatureWhile being cooled with ice
  11. extractionextracted with toluene
  12. extractionThe extract was extracted with 10% sodium hydroxide aqueous 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-55489fceb40d443396d435d68f2c97da
Source dataset
uspto-grants-2000_07
Patent number
US06083987

Reaction notes

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