Ethylparaben → HCID 19890431, compound

HRID 893542Notes

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.[Na].[H-]>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

Conditions

Temperature: 130 °C

Procedure

0.54 g of 3-trifluoromethylheptyl p-toluenesulfonate obtained in Step 1), 0.27 g of ethyl p-hydroxybenzoate and 1 ml of dimethylformamide (DMF) were placed in a round-bottomed flask, and 0.07 g of sodium 60%-hydride was added thereto together with DMF, followed by 6 hours of stirring at 130° C. After the reaction, DMF was distilled off under a reduced pressure, and water was added, followed by extraction with diethyl ether. The ether solution was dried with sodium sulfate, followed by distilling-off of the solvent to obtain 0.62 g of a crude product. The crude product was then purified by thin layer chromatography with benzene as the developer to obtain 0.22 g of ethyl p-(3-trifluoromethylheptyloxy)benzoate (yield: 42%).

Workup

distillationwas distilled off under a reduced pressure, and water
additionwas added
extractionfollowed by extraction with diethyl ether
dry with materialThe ether solution was dried with sodium sulfate
customto obtain 0.62 g of a crude product
customThe crude product was then purified by thin layer chromatography with benzene as the developer

Sources & evidence

ORD record: ord-b24b2185bfd44cacbbe3152e807ab4ac
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05126071

Reaction notes

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