Hydrochloric Acid → 2-Cyano-2-methylhexyl p-toluenesulfonate

HRID 1461197Notes

Reaction equation

HRID 1461197 reaction equation
[C:1]([C:3]([CH3:10])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][OH:5])#[N:2].[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>[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17]([O:5][CH2:4][C:3]([C:1]#[N:2])([CH3:10])[CH2:6][CH2:7][CH2:8][CH3:9])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 14793448(+)-2-Cyano-2-methylhexanol

Product 1

HCID 147934682-Cyano-2-methylhexyl p-toluenesulfonateYield 66.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

535 mg (3.8 mM) of (+)-2-cyano-2-methylhexanol ([α]D26 +0.66 degree (c 1.823, ether)) and 911 mg (11.4 mM) of dry pyridine were stirred at room temperature, and 724 mg (3.8 mM) of p-toluenesulfonyl chloride was added thereto, followed by 7 hours of reaction. After the reaction, 3 ml of 2N-hydrochloric acid was added thereto, followed by extraction with diethyl ether. the resultant organic layer was washed with a small amount of 2N-hydrochloric acid and distilled water, followed by drying on sodium sulfate, distilling-off of the solvent and purification by silica gel column chromatography (developer solvent: methylene chloride) to obtain 748 mg of 2-cyano-2-methylhexyl p-toluenesulfonate (yield: 63.3%).

Workup

  1. customfollowed by 7 hours of reaction
  2. additionwas added
  3. extractionfollowed by extraction with diethyl ether
  4. washthe resultant organic layer was washed with a small amount of 2N-hydrochloric acid
  5. distillationdistilled water
  6. dry with materialby drying on sodium sulfate, distilling-off of the solvent and purification by silica gel column chromatography (developer solvent: methylene chloride)

Sources & evidence

ORD record
ord-6822a78bd2b242188077eb579b669849
Source dataset
uspto-grants-1991_12
Patent number
US05075031

Reaction notes

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