Dimethyl Sulfoxide → HCID 13563074, compound

HRID 867617Notes

Reaction equation

HRID 867617 reaction equation
CS(C)=O.[CH2:5]([O:12][CH:13]([CH2:16][OH:17])[CH2:14][OH:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:18](Br)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[OH-].[K+]>O.C1COCC1>[CH2:18]([O:17][CH2:16][CH:13]([CH2:14][O:15][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[O:12][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81401-BromooctaneHCID 14797Potassium HydroxideHCID 2035672-(Phenylmethoxy)-1,3-propanediol

Product 1

HCID 13563074HCID 13563074, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixed solution consisting of 50 ml of DMSO and 30 ml of THF were dissolved 3.64 g (20 mmole) of 2-benzylglycerin and 9.26 g (48 mmole) of octyl bromide, and 8.96 g (160 mmole) of powdered potassium hydroxide was added to the solution, followed by vigorous stirring. Two hours later, the reaction solution was poured in cold water, and the mixture was extracted with n-hexane. The extract was washed with water, dried and concentrated, followed by purification by silica-gel chromatography (eluent: n-hexane-ethyl acetate, 20:1) to give 6.22 g (77%) of the desired compound as colorless liquid.

Workup

  1. additionwas added to the solution
  2. extractionthe mixture was extracted with n-hexane
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customfollowed by purification by silica-gel chromatography (eluent: n-hexane-ethyl acetate, 20:1)

Sources & evidence

ORD record
ord-181b8d2a8aa344d59e03498c170e3836
Source dataset
uspto-grants-1988_10
Patent number
US04775758

Reaction notes

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