Ethylparaben → Benzoic acid, 4-[(3-methyl-2-butenyl)oxy]-, ethyl ester

HRID 1625305Notes

Reaction equation

HRID 1625305 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.C(=O)([O-])[O-].[K+].[K+].[CH3:19][C:20]([CH3:24])=[CH:21][CH2:22]Cl>C(#N)C>[CH3:19][C:20]([CH3:24])=[CH:21][CH2:22][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

5

Reactant 3

HCID 8434EthylparabenHCID 104291-Chloro-3-methyl-2-buteneHCID 11430Potassium Carbonate

Product 1

HCID 13203109Benzoic acid, 4-[(3-methyl-2-butenyl)oxy]-, ethyl esterYield 95.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 4-hydroxybenzoate (1.66 g, 10.0 mmol) and anhydrous potassium carbonate (2.07 g, 15.0 mmol) in acetonitrile (30 ml) was treated with 3-methyl-2-butenyl chloride (1.35 ml, 12.0 mmol) and the mixture was stirred and held at reflux for 3 hours. Upon cooling the solvent was removed in vacuo and the mixture partitioned between dichloromethane and water. The organics were separated and the solvent removed in vacuo to afford ethyl 4-(3-methyl-but-2-enyloxy)-benzoate (2.23 g, 95%) as a pale yellow liquid which was used without further purification. 1H NMR (DMSO-d6) 7.89 (2H, d), 7.04 (2H, d), 5.44 (1H, t), 4.62 (2H, d), 4.28 (2H, q), 1.77 (3H, s), 1.73 (3H, s), 1.31 (3H, t). MS: [M+H]+ 235.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureUpon cooling the solvent
  3. customwas removed in vacuo
  4. customthe mixture partitioned between dichloromethane and water
  5. customThe organics were separated
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-aee3e858dc374403ace9cd58b35b0be7
Source dataset
uspto-grants-2014_07
Patent number
US08779132B2

Reaction notes

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