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

HRID 644588Notes

Reaction equation

HRID 644588 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 separtaed 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 solvent removed in vacuo

Sources & evidence

ORD record
ord-24bb095c8c3c4942b302ffe467395439
Source dataset
uspto-grants-2010_04
Patent number
US07700625B2

Reaction notes

Loading…