4-Toluenesulfonyl chloride → 5-Hexen-1-ol, 1-(4-methylbenzenesulfonate)

HRID 461838Notes

Reaction equation

HRID 461838 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.[CH2:12]([OH:18])[CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17]>N1C=CC=CC=1>[S:7]([O:18][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17])([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 699635-Hexen-1-ol

Product 1

HCID 110759995-Hexen-1-ol, 1-(4-methylbenzenesulfonate)

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In this preparation 1.0 mole of p-toluenesulfonyl chloride is dissolved in 700 ml. of pyridine at 0° C, under nitrogen, and then 1.0 mole of hex-5-en-1-ol is added dropwise. The mixture is then stirred at room temperature for 16 hours, then poured into ice water and extracted with ethyl ether. The ethyl ether extract is then sequentially washed with water, 10% aqueous hydrochloric acid, water, aqueous 10% sodium bicarbonate solution and water, and then dried over magnesium sulfate and filtered. The filtrate is evaporated to dryness, under vacuum, affording hex-5-en-1-ol tosylate as a residue.

Workup

  1. dissolutionis dissolved in 700 ml
  2. extractionextracted with ethyl ether
  3. extractionThe ethyl ether extract
  4. washis then sequentially washed with water, 10% aqueous hydrochloric acid, water, aqueous 10% sodium bicarbonate solution and water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate is evaporated to dryness, under vacuum

Sources & evidence

ORD record
ord-eb9e5b3bcdb14d5bb36f205ee857c098
Source dataset
uspto-grants-1977_12
Patent number
US04064259

Reaction notes

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