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

HRID 1391171Notes

Reaction equation

HRID 1391171 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 2N 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 2N hydrochloric acid and water
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent is distilled in vacuo

Sources & evidence

ORD record
ord-3040c01831e542bd9a2cdc0ccb443555
Source dataset
uspto-grants-1979_02
Patent number
US04140861

Reaction notes

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