Hydrochloric Acid → HCID 19102388, compound

HRID 2073429Notes

Reaction equation

HRID 2073429 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-ba1d2b19bae54c09997b91fd6b175807
Source dataset
uspto-grants-1990_04
Patent number
US04917817

Reaction notes

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