4-Toluenesulfonyl chloride → HCID 18411913, compound

HRID 896526Notes

Reaction equation

HRID 896526 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[CH:5][CH:4]=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>N1C=CC=CC=1>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][S:20]([C:17]2[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=2)(=[O:22])=[O:21])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 112755102-(4-(Trifluoromethyl)phenyl)ethan-1-ol

Product 1

HCID 18411913HCID 18411913, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-(4-trifluoromethylphenyl)-ethanol (570 mg, 3.0 mmol) in pyridine (6 mL) was stirred on an ice/acetone bath and treated with p-toluenesulfonyl chloride (630 mg, 3.3 mmol). The cooling bath was replaced with an ice/water bath and the mixture was stirred for 3.5 hours. Ice-cold water (12 mL) was added slowly, and the mixture was extracted three times with chloroform. The combined organic phases were washed with water, then with cold 1.0 N aqueous sulfuric acid until the wash phase was acidic. The organic phase was dried over sodium sulfate and concentrated to provide a white solid (826 mg) which contained about 10% by weight of residual alcohol. This was used without further purification. 1H NMR (300 MHz, CDCl3) for toluenesulfonate: δ7.65 (d, J=8 Hz, 2H), 7.50 (d, J=8 Hz, 2H), 7.26 (d, J=8 Hz, 2H), 7.23 (d, J=8 Hz, 2H), 4.26 (t, J=7 Hz, 2H), 3.02 (t, J=7 Hz, 2H), 2.44 (s, 3H).

Workup

  1. customThe cooling bath was replaced with an ice/water bath
  2. extractionthe mixture was extracted three times with chloroform
  3. washThe combined organic phases were washed with water
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ade26f5432b84c6bb841dbadd5e0ba2d
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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