4-Toluenesulfonyl chloride → 2-(2-Tosyloxyethyl)-1,4-benzodioxan

HRID 1032404Notes

Reaction equation

HRID 1032404 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH2:13][CH2:14][CH:15]1[O:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[O:17][CH2:16]1>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:12][CH2:13][CH2:14][CH:15]2[O:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[O:17][CH2:16]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 98334Ethanol, 2-(1,4-benzodioxan-2-yl)-

Product 1

HCID 128505822-(2-Tosyloxyethyl)-1,4-benzodioxanYield 77.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

12.20 g (64 mmol) of p-toluenesulphonyl chloride are added at room temperature and while stirring to a solution of 10.81 g (60 mmol) of 2-(2-hydroxyethyl)benzo-1,4-dioxan in 35 ml of absolute pyridine, the slightly exothermic reaction being maintained at room temperature by means of an ice bath. The reaction mixture is stirred for a further 3 hours at room temperature and then poured onto ice-water. The crystals formed are filtered off with suction, washed with water and dried in vacuo. 15.50 g (77.2%) of 2-[2-(p-toluenesulphonyloxy)ethyl]-benzo-1,4-dioxan, which melts at 82°-84°, are obtained.

Workup

  1. customthe slightly exothermic reaction
  2. additionpoured onto ice-water
  3. customThe crystals formed
  4. filtrationare filtered off with suction
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-1c2fe97fcde34629b2679411d7cdd5a0
Source dataset
uspto-grants-1990_09
Patent number
US04957928

Reaction notes

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