Ethylparaben → HCID 19890428, compound

HRID 893545Notes

Reaction equation

C1(C)C=CC(S(O[CH2:11][CH2:12][CH:13]([C:20]([F:23])([F:22])[F:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])(=O)=O)=CC=1.[OH:25][C:26]1[CH:36]=[CH:35][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:27]=1.[H-].[Na+]>CN(C=O)C>[F:21][C:20]([F:22])([F:23])[CH:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:11][O:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:35][CH:36]=1

Participants

Conditions

Temperature: 130 °C

Procedure

345 mg of 3-trifluoromethylnonyl p-toluenesulfonate obtained in Step 1), 166 mg of ethyl p-hydroxybenzoate and 1 ml of dimethylformamdie (DMF) were placed in a round-bottomed flask, and 80 mg of sodium hydride (60%) 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 methylene chloride. The methylene chloride solution was dried with magnesium sulfate, followed by distilling-off of the solvent and purification by thin layer chromatography with benzene as the developer to obtain 205 mg of ethyl p-(3-trifluoromethylnonyloxy)-benzoate (yield: 60.5%).

Workup

distillationwas distilled off under a reduced pressure, and water
additionwas added
extractionfollowed by extraction with methylene chloride
dry with materialThe methylene chloride solution was dried with magnesium sulfate
distillationfollowed by distilling-off of the solvent and purification by thin layer chromatography with benzene as the developer

Sources & evidence

ORD record: ord-9101d0bb7337457bba65bfe9f50c42ad
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05126071

Reaction notes

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