Ethylparaben → HCID 14549135, compound

HRID 863360Notes

Reaction equation

HRID 863360 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21])(=O)=O)=CC=1.[OH:23][C:24]1[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=1.[H-].[Na+]>CN(C)C=O>[CH2:21]([O:23][C:24]1[CH:25]=[CH:26][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:33][CH:34]=1)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[CH2:11]

Participants

5

Reactant 3

HCID 8434EthylparabenHCID 24758Sodium hydrideHCID 11141895HCID 11141895, compound

Product 1

HCID 14549135HCID 14549135, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6 ml of dimethylformamide was added to 6.20 g (19.1 mM) of 10-undecenyl p-toluenesulfonate and 3.17 g (19.1 mM) of ethyl p-hydroxybenzoate, followed by sufficient stirring. Into the resultant solution was added 0.77 g (19.3 mM) of sodium hydride (60%), followed by heat-refluxing for 7 hours. After the reaction, dimethylformamide was distilled off, followed by addition of water and extraction with ether. To the ether extract liquid was added anhydrous sodium sulfate for drying, followed by distilling-off of the ether and separation-purification by column chromatography (developer solvent: methylene chloride) to obtain 5.80 g (18.2 mM) of ethyl p-(10-undecenyl)oxybenzoate. Yield: 91.2%.

Workup

  1. temperatureby heat-refluxing for 7 hours
  2. distillationwas distilled off
  3. additionfollowed by addition of water and extraction with ether
  4. extractionTo the ether extract liquid
  5. additionwas added anhydrous sodium sulfate
  6. customfor drying
  7. distillationfollowed by distilling-off of the ether and separation-purification by column chromatography (developer solvent: methylene chloride)

Sources & evidence

ORD record
ord-99579ead58cd4807acfde06c20561c8a
Source dataset
uspto-grants-1998_02
Patent number
US05720898

Reaction notes

Loading…