4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid Chroman-3-ylmethyl ester

HRID 1032383Notes

Reaction equation

HRID 1032383 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][CH:14]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[O:16][CH2:15]1>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:12][CH2:13][CH:14]2[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[O:16][CH2:15]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 27954603,4-dihydro-2H-chromen-3-ylmethanol

Product 1

HCID 11267124Toluene-4-sulfonic acid Chroman-3-ylmethyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

46.14 g (242 mmol) of p-toluenesulphonyl chloride are added while stirring at room temperature to a solution of 36.12 g (220 mmol) of 3-hydroxymethylchroman in 100 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. 65.84 g (94%) of 3-(p-toluenesulphonyloxymethyl)chroman having a melting point of 86°-87° 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-7716e46dbf6f402992231a0269cb22cb
Source dataset
uspto-grants-1990_09
Patent number
US04957928

Reaction notes

Loading…