Water → 4-Acetoxy-5-propoxy-1-pentanol Tosylate

HRID 26607Notes

Reaction equation

HRID 26607 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.[C:12]([O:15][CH:16]([CH2:21][O:22][CH2:23][CH2:24][CH3:25])[CH2:17][CH2:18][CH2:19][OH:20])(=[O:14])[CH3:13].O>N1C=CC=CC=1.CCOCC>[S:7]([O:20][CH2:19][CH2:18][CH2:17][CH:16]([O:15][C:12](=[O:14])[CH3:13])[CH2:21][O:22][CH2:23][CH2:24][CH3:25])([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

6

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 20386043HCID 20386043, compound

Product 1

HCID 538286304-Acetoxy-5-propoxy-1-pentanol Tosylate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

A solution of p-toluenesulfonyl chloride (42.0 g., 0.22 mole) in pyridine (100 ml.) is cooled in an ice bath while 4-acetoxy-5-propoxy-1-pentanol (36.8 g., 0.193 mole) is added dropwise with stirring during 40 minutes. The ice bath is replaced by a cool (20° C.) water bath and stirring is continued for 2 hours. The mixture is then poured into 500 ml. of water. The oily product is taken up in ether, washed with 2 N hydrochloric acid and water, and dried over sodium sulfate. The solvent is distilled in vacuo to leave the crude title compound as a yellow oil.

Workup

  1. additionis added dropwise
  2. stirringstirring
  3. waitis continued for 2 hours
  4. additionThe mixture is then poured into 500 ml
  5. washwashed with 2 N hydrochloric acid and water
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent is distilled in vacuo

Sources & evidence

ORD record
ord-b89920586d3d46de92fce96a21b4f5eb
Source dataset
uspto-grants-1979_04
Patent number
US04150235

Reaction notes

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