4-Toluenesulfonyl chloride → HCID 131710165, compound

HRID 1606692Notes

Reaction equation

HRID 1606692 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([OH:13])[CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[C:25]1([CH3:47])[CH:30]=[CH:29][C:28]([S:31]([O:34]C(CC)COCC2C=CC=CC=2)(=[O:33])=[O:32])=[CH:27][CH:26]=1>N1C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH:10]([OH:13])[CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:47][C:25]1[CH:30]=[CH:29][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 5617991-(Benzyloxy)butan-2-olHCID 21544367HCID 21544367, compound

Product 1

HCID 131710165HCID 131710165, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1,000 g. (5.45 mole) of 1-benzyloxy-2-butanol in 2,000 ml. of pyridine, 1,170 g. (6.04 mole) of p-toluenesulfonyl chloride is added in small portions for a period of about 30 minutes at room temperature. During the addition the temperature raises, but it is kept at the room values by cooling the reaction mixture by an external circulation of ice-water; then the solution is vigorously stirred always at room temperature for about 16-20 hours. After cooling to 0°C, the solution is poured into ice-water and an oil precipitates, which is separated from the aqueous phase by decantation. The remaining water portion is twice extracted with benzene; then the oily and the benzene phases are combined together and the resulting benzene solution is cooled to about 10°C. Said organic solution is subsequently washed with concentrated hydrochloric acid, then with a saturated solution of sodium bicarbonate and finally with water, and dried over sodium sulfate. After distillation of the solvent a residue is obtained which is 1-benzyloxy-2-butanol p-toluenesulfonate which decomposes upon distillation. Yield of this step: 100%.

Workup

  1. additionDuring the addition the temperature
  2. temperatureraises
  3. temperatureAfter cooling to 0°C
  4. customan oil precipitates
  5. customwhich is separated from the aqueous phase by decantation
  6. extractionThe remaining water portion is twice extracted with benzene
  7. temperaturethe resulting benzene solution is cooled to about 10°C
  8. washis subsequently washed with concentrated hydrochloric acid
  9. dry with materialwith a saturated solution of sodium bicarbonate and finally with water, and dried over sodium sulfate
  10. distillationAfter distillation of the solvent a residue
  11. customis obtained which
  12. distillationdecomposes upon distillation

Sources & evidence

ORD record
ord-8a924c00260b4d5ebc05a9ed461c006f
Source dataset
uspto-grants-1976_04
Patent number
US03953513

Reaction notes

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