Thionyl Chloride → 10-Benzyloxy-1-chlorodecane

HRID 2290807

Reaction equation

HRID 2290807 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:22])=O>CN(C)C=O>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][Cl:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 110108641-Decanol, 10-(phenylmethoxy)-

Product 1

HCID 1106593210-Benzyloxy-1-chlorodecane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7 g of 10-benzyloxy-1-decanol, 8 ml of thionyl chloride, and 0.2 ml of dimethylformamide was heated to 50° to 60° C. for one hour. After the reaction was over, the reaction mixture was concentrated under reduced pressure, the residue was dissolved in 50 ml of n-hexane, and after washing the solution with water, the solution was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off and the residue was applied to silica gel column chromatography and eluted with toluene to provide 6.7 g of oily 10-benzyloxy-1-chlorodecane. Boiling point 135°-140° C. (0.6-0.9 mm Hg).

Workup

  1. temperaturewas heated to 50° to 60° C. for one hour
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in 50 ml of n-hexane
  4. washafter washing the solution with water
  5. dry with materialthe solution was dried over anhydrous magnesium sulfate
  6. distillationThen, the solvent was distilled off
  7. washeluted with toluene

Sources & evidence

ORD record
ord-c368d9fdd8dc4700bb4ebdb9d900c8f9
Source dataset
uspto-grants-1986_10
Patent number
US04618627

Linked notes

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