Water → 3-(Tetradecyloxy)propan-1-ol

HRID 2295841Notes

Reaction equation

HRID 2295841 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[CH2:6](Br)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH-].[K+].O>CS(C)=O.O1CCCC1>[CH2:19]([O:4][CH2:3][CH2:2][CH2:1][OH:5])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8208Myristyl bromideHCID 104421,3-PropanediolHCID 14797Potassium Hydroxide

Product 1

HCID 1142393-(Tetradecyloxy)propan-1-olYield 34.6%

Reagents, catalysts & solvents 1

HCID 21830753dimethylsulfoxide THFSolvent

Procedure

In 70 ml of a mixture of dimethylsulfoxide-tetrahydrofuran (1:1) are dissolved 12.3 g of trimethylene glycol and 15 g of tetradecyl bromide. To the solution is added 12 g of powdery potassium hydroxide. The mixture is vigorously stirred for one hour at a room temperature, which is refluxed under heating for two hours. The reaction mixture is poured into 400 ml of cold water, which is neutralized and subjected to extraction with ethyl acetate, then washed with water and dried. The resultant is concentrated to dryness, and the residue is dissolved in methanol when hot. Cooling of the solution gives precipitation of crystals, which are removed by filtration. The filtrate is refined by means of chromatography employing silica-gel (eluent: chloroform) to give 5.1 g of the end-product.

Workup

  1. temperaturewhich is refluxed
  2. temperatureunder heating for two hours
  3. extractionsubjected to extraction with ethyl acetate
  4. washwashed with water
  5. customdried
  6. concentrationThe resultant is concentrated to dryness
  7. dissolutionthe residue is dissolved in methanol when hot
  8. temperatureCooling of the solution
  9. customgives
  10. customprecipitation of crystals, which
  11. customare removed by filtration

Sources & evidence

ORD record
ord-f3c79f0c2ea14f1d9716cde923ae6315
Source dataset
uspto-grants-1984_01
Patent number
US04426525

Reaction notes

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