4-Toluenesulfonyl chloride → 8-Azido-1-octanol

HRID 5126

Reaction equation

HRID 5126 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[N-:22]=[N+:23]=[N-:24].[Na+].C(OCC)(=O)C>N1C=CC=CC=1.C(Cl)Cl.CN(C)C=O>[N:22]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9])=[N+:23]=[N-:24]

Participants

8

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 694201,8-Octanediol

Product 1

HCID 117896658-Azido-1-octanol

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

14.65 g of 1,8-octanediol was dissolved in 80 g of pyridine, and cooled to 10° C. A solution of 19 g p-toluenesulfonyl chloride in 70 ml anhydrous methylene chloride was added dropwise thereto, and the mixture was heated gradually overnight for reaction. After water washing, the solvent was removed by distillation, to produce an oily residue. The residue was dissolved in dimethylformamide to a 200 ml solution, to which was added 20 g of sodium azide, and the resultant mixture was maintained at 80° C. for 2 hours for reaction. The mixture was, after added with ethyl acetate, was washed with water 4 times and the solvent was removed by distillation. The object compound was isolated by silica-gel column-chromatography (CHCl3 -AcOEt 5:1-1:1) The yield was 6.07 g.

Workup

  1. temperaturethe mixture was heated gradually overnight for reaction
  2. customAfter water washing, the solvent was removed by distillation
  3. customto produce an oily residue
  4. washwas washed with water 4 times
  5. customthe solvent was removed by distillation
  6. customThe object compound was isolated by silica-gel column-chromatography (CHCl3 -AcOEt 5:1-1:1) The yield was 6.07 g

Sources & evidence

ORD record
ord-86a11031d1d743c286db830c75a75df3
Source dataset
uspto-grants-1993_09
Patent number
US05243035

Linked notes

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