Ethylparaben → HCID 19890431, compound

HRID 1460935Notes

Reaction equation

HRID 1460935 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH:13]([C:18]([F:21])([F:20])[F:19])[CH2:14][CH2:15][CH2:16][CH3:17])(=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>[F:19][C:18]([F:20])([F:21])[CH:13]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:12][CH2:11][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

Participants

5

Reactant 3

HCID 8434EthylparabenHCID 24758Sodium hydrideHCID 14533171HCID 14533171, compound

Product 1

HCID 19890431HCID 19890431, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In a round-bottomed flask, 0.88 g of the 3-trifluoromethylheptyl p-toluenesulfonate 2, 0.4 g of ethyl p-hydroxybenzoate and 1 ml of dimethylformamide were placed, and 50 mg of sodium hydride was added thereto, followed by 8 hours of heat-refluxing and 15 hours of standing at room temperature. After the reaction, dimethylformamide was distilled off, and dilute hydrochloric acid was added to the product, which was then extracted with methylene chloride. The resultant organic layer was washed with water and dried with magnesium sulfate, followed by distilling-off of the solvent and purification by thin layer chromatography (developer: methylene chloride/ hexane=1/1) to obtain 0.7 g of ethyl p-(3-trifluoromethylheptyloxy)benzoate 3. (Yield: 80%)

Workup

  1. temperatureof heat-refluxing and 15 hours
  2. customof standing at room temperature
  3. distillationwas distilled off
  4. additiondilute hydrochloric acid was added to the product, which
  5. extractionwas then extracted with methylene chloride
  6. washThe resultant organic layer was washed with water
  7. dry with materialdried with magnesium sulfate
  8. distillationfollowed by distilling-off of the solvent and purification by thin layer chromatography (developer: methylene chloride/ hexane=1/1)

Sources & evidence

ORD record
ord-0d93dd20d3574c51ba2ff48c53d014da
Source dataset
uspto-grants-1991_12
Patent number
US05073306

Reaction notes

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