4-Toluenesulfonyl chloride → HCID 19853898, compound

HRID 1722639Notes

Reaction equation

HRID 1722639 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][OH:11].[S:12](Cl)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]>C(Cl)Cl>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][O:11][S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 2667422-(3-hydroxypropyl)phenol

Product 1

HCID 19853898HCID 19853898, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 79.2 g of the diol from Example 2 in 400 ml of methylene chloride is added 100 ml of tiethylamine, followed by 91 g of tosyl chloride in 200 ml methylene chloride. The reaction mixture is stirred at room temperature overnight. The salts are then filtered off and the mixture washed with water, brine and water. The organic layer is dried (MgSO4), filtered and concentrated to obtain 3-(o-hydroxyphenyl)-1-tosyloxypropane as a light brown oil which is used directly in the next step.

Workup

  1. filtrationThe salts are then filtered off
  2. washthe mixture washed with water, brine and water
  3. dry with materialThe organic layer is dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-654cb79b8af94fcc9dccc60314062166
Source dataset
uspto-grants-1989_08
Patent number
US04857517

Reaction notes

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