4-Toluenesulfonyl chloride → HCID 9858183, compound

HRID 1196029Notes

Reaction equation

HRID 1196029 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][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[O: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][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[O:15]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 27948162-(Hydroxymethyl)chroman

Product 1

HCID 9858183HCID 9858183, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

38.16 g (0.2 mol) of p-toluenesulphonyl chloride are added at room temperature while stirring to a solution of 31 g (0.189 mol) of 2-hydroxymethylchroman in 110 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 oil which separates out is removed by decanting the aqueous phase, dissolved in diethyl ether and washed with ice-cold 2N hydrochloric acid and ice-water. The ethereal phases are dried over sodium sulphate and concentrated by evaporation in vacuo. 58.15 g (96.6%) of 2-(p-toluenesulphonyloxymethyl)chroman are obtained in the form of a colourless oil.

Workup

  1. customthe slightly exothermic reaction
  2. additionpoured onto ice-water
  3. customThe oil which separates out is removed
  4. customby decanting the aqueous phase
  5. dissolutiondissolved in diethyl ether
  6. washwashed with ice-cold 2N hydrochloric acid and ice-water
  7. dry with materialThe ethereal phases are dried over sodium sulphate
  8. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-fdffeedb3df44a68890ad83a56446dc3
Source dataset
uspto-grants-1992_05
Patent number
US05112855

Reaction notes

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