Hydrochloric Acid → HCID 19102388, compound

HRID 893544Notes

Reaction equation

HRID 893544 reaction equation
[F:1][C:2]([F:14])([F:13])[CH:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:4][CH2:5][OH:6].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.Cl>N1C=CC=CC=1>[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21]([O:6][CH2:5][CH2:4][CH:3]([C:2]([F:13])([F:14])[F:1])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 14533173HCID 14533173, compound

Product 1

HCID 19102388HCID 19102388, compoundYield 6,488.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.08 mg of 3-trifluoromethyl-1-nonanol was dissolved in 453 mg of pyridine, and the solution was cooled with ice, followed by addition of 276 mg of p-toluenesulfonic chloride, stirring for 2 hours under cooling with ice and stirring overnight at room temperature. After the reaction, the product was acidified with 2N-hydrochloric acid and extracted with diethyl ether. The resultant diethyl ether solution was washed with water and dried with magnesium sulfate, and the solvent was distilled off. The crude product was purified by thin layer chromatography with benzene as the developer to obtain 345 mg (yield: 65%) of 3-trifluoromethylnonyl p-toluenesulfonate, which showed: [α]D28 +1.63 (c 5.04, CHCl3).

Workup

  1. temperaturethe solution was cooled with ice
  2. temperatureunder cooling with ice
  3. stirringstirring overnight at room temperature
  4. customAfter the reaction
  5. extractionextracted with diethyl ether
  6. washThe resultant diethyl ether solution was washed with water
  7. dry with materialdried with magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customThe crude product was purified by thin layer chromatography with benzene as the developer

Sources & evidence

ORD record
ord-fcdbea67a6e94777b239b7d697b6639c
Source dataset
uspto-grants-1992_06
Patent number
US05126071

Reaction notes

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