4-Toluenesulfonyl chloride → 3-[2-(p-Toluenesulphonyloxy)ethyl]chroman

HRID 1032393Notes

Reaction equation

HRID 1032393 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[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=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[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[O:17][CH2:16]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 148384142-(3,4-dihydro-2H-1-benzopyran-3-yl)ethan-1-ol

Product 1

HCID 148384153-[2-(p-Toluenesulphonyloxy)ethyl]chromanYield 59.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6.29 g (33 mmol) of p-toluenesulphonyl chloride are added while stirring at room temperature to a solution of 5.35 g (30 mmol) of 3-(2-hydroxyethyl)chroman in 30 ml of absolute pyridine, the slightly exothermic reaction being maintained at room temperature by means of an ice bath. After stirring for a further three hours at room temperature, the reaction mixture is poured onto ice-water. The crystals formed are filtered off with suction, washed with water and dried in vacuo. 5.9 g (59.2%) of 3-[2-(p-toluenesulphonyloxy)ethyl]chroman, which melts at 91°-93°, are obtained.

Workup

  1. customthe slightly exothermic reaction
  2. additionthe reaction mixture is poured 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-19a26f9f3ccd45fd85638e530df71ca0
Source dataset
uspto-grants-1990_09
Patent number
US04957928

Reaction notes

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