4-Toluenesulfonyl chloride → 4-(2-Tosyloxyethyl)phenol

HRID 565128Notes

Reaction equation

HRID 565128 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.[S:11](Cl)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12]>N1C=CC=CC=1>[S:11]([O:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=1)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 10393Tyrosol

Product 1

HCID 114605544-(2-Tosyloxyethyl)phenolYield 59%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Hydroxyphenethyl alcohol (3.2 g) was dissolved in 50 ml of pyridine, to which 4.0 g of tosyl chloride was added in small portions under ice cooling. The temperature of the reaction mixture was allowed to rise to room temperature, at which it was stirred for 2 hours. Then, insoluble matter was filtered off, and pyridine was distilled off under reduced pressure. The residue was isolated and purified by chromatography on a silica gel column (eluent: CHCl3), whereby 3.4 g of the compound (1) were obtained (yield: 59%).

Workup

  1. additionwas added in small portions under ice cooling
  2. customto rise to room temperature, at which it
  3. filtrationThen, insoluble matter was filtered off
  4. distillationpyridine was distilled off under reduced pressure
  5. customThe residue was isolated
  6. custompurified by chromatography on a silica gel column (eluent: CHCl3)

Sources & evidence

ORD record
ord-a3631539477b425a86b9caad9636a790
Source dataset
uspto-grants-2001_01
Patent number
US06171520B2

Reaction notes

Loading…