Water → Isopropyl tosylate

HRID 910753Notes

Reaction equation

HRID 910753 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][CH:13]([OH:15])[CH3:14].O>N1C=CC=CC=1>[CH:13]([O:15][S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])([CH3:14])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 3776IsopropanolHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 598985Isopropyl tosylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., 4-methyl-benzenesulfonyl chloride (3.8 g) was added to a solution of 2-propanol (6.12 ml) in pyridine (6.6 ml). The reaction mixture was stirred at 0° C. for 2 h and then at 20° C. for 16 h. The reaction mixture was poured into water (150 ml) and extracted with dichloromethane. The combined organic phases were washed with 3M aqueous HCl and sat. NaHCO3. After drying (MgSO4) and concentrating in vacuo, the title product was obtained as a pale yellow oil. Yield: 2.89 g. MS-ESI: [M+H]+=215.

Workup

  1. waitat 20° C. for 16 h
  2. extractionextracted with dichloromethane
  3. washThe combined organic phases were washed with 3M aqueous HCl and sat. NaHCO3
  4. dry with materialAfter drying (MgSO4)
  5. concentrationconcentrating in vacuo

Sources & evidence

ORD record
ord-088c27dfaa8b4cdf8aee01d3422a58e2
Source dataset
uspto-grants-2011_09
Patent number
US08022218B2

Reaction notes

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