4-Toluenesulfonyl chloride → 2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

HRID 2110394Notes

Reaction equation

HRID 2110394 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH3:12][C:13]1([CH3:20])[O:17][CH:16]([CH2:18][OH:19])[CH2:15][O:14]1>N1C=CC=CC=1.CCOCC>[C:7]1([CH3:8])[CH:9]=[CH:10][C:4]([S:1]([O:19][CH2:18][CH:16]2[CH2:15][O:14][C:13]([CH3:20])([CH3:12])[O:17]2)(=[O:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 7528Solketal

Product 1

HCID 2350972,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

57.2 g (300 mmol) of tosyl chloride are added to a solution of 39.6 g (300 mmol) of (2,2-dimethyl[1,3]dioxolan-4-yl)methanol in 170 ml of pyridine at 0° C. The mixture is stirred overnight, diluted with ether, washed with a 1N hydrochloric acid solution until the aqueous phase is at acid pH, and then washed with a saturated sodium hydrogen carbonate solution.

Workup

  1. washwashed with a 1N hydrochloric acid solution until the aqueous phase
  2. washwashed with a saturated sodium hydrogen carbonate solution

Sources & evidence

ORD record
ord-49b8e048cf124c7aa42a5f8c39847703
Source dataset
uspto-grants-2009_04
Patent number
US07517907B2

Reaction notes

Loading…