Hydrochloric Acid → HCID 14297706, compound

HRID 2254498Notes

Reaction equation

HRID 2254498 reaction equation
[F:1][CH:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][OH:4].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.Cl>N1C=CC=CC=1>[F:1][CH:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][O:4][S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 130224002-Fluorooctan-1-ol

Product 1

HCID 14297706HCID 14297706, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 6.7 g of 2-fluorooctanol in 25 ml of pyridine, a solution of 10.4 g of p-toluenesulfonyl chloride in 40 ml of pyridine was added dropwise in 20 minutes below 0° C. on an ice water bath, followed by stirring for 7 hours at room temperature. After the reaction, the reaction mixture was poured into 200 ml of ice water and acidified with 6N-hydrochloric acid aqueous solution, followed by extraction with methylene chloride. The organic layer was washed with water and dried with anhydrous magnesium sulfate, followed by distilling-off of the solvent to precipitate a crystal. The crystal was purified by silica gel column chromatography to obtain 12.7 g of 2-fluorooctyl-p-toluenesulfonate.

Workup

  1. customAfter the reaction
  2. extractionfollowed by extraction with methylene chloride
  3. washThe organic layer was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customto precipitate a crystal
  6. customThe crystal was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-afd4b104df5f46eebae213cfa411146a
Source dataset
uspto-grants-1993_08
Patent number
US05236619

Reaction notes

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