4-Toluenesulfonyl chloride → 1472-00-0
Reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][C@@H:5]([CH2:8][OH:9])[O:4]1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>N1C=CC=CC=1>[S:16]([O:1][CH2:2][C@H:3]1[CH2:7][CH2:6][C@@H:5]([CH2:8][O:9][S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[O:4]1)([C:13]1[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=1)(=[O:18])=[O:17]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
To a three-neck flask equipped with a thermometer, reflux condenser, mechanical stirrer, and dropping funnel a solution of 924 grams (7 moles) of cis-2,5-bis-(hydroxymethyl) tetrahydrofuran, represented by formula (I), in 900 ml of pyridine was placed and cooled at 5° C. A solution of 2669 grams (14 moles) of p-toluenesulfonyl chloride in 4 liters of pyridine was added slowly through the dropping funnel. The temperature during the addition was kept below 10°-15° C. After the addition of p-toluenesulfonyl chloride, the reaction mixture was stirred for 2 hours and then let stand at room temperature overnight. The reaction mixture was poured over ice-water and the product precipitated. The ditosylate, represented by formula (II), was filtered off and washed several times with water and dried. The product obtained had a melting point of 125°-126.5° C.
Workup
- customTo a three-neck flask equipped with a thermometer
- temperaturereflux condenser, mechanical stirrer
- additionThe temperature during the addition
- customwas kept below 10°-15° C
- waitlet stand at room temperature overnight
- customthe product precipitated
- filtrationwas filtered off
- washwashed several times with water
- customdried
- customThe product obtained
Sources & evidence
- ORD record
- ord-85e64ef16c43445daa106ad7525e5285
- Source dataset
- uspto-grants-1976_04
- Patent number
- US03953596
Reaction notes
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