Dimethyl Sulfoxide → 4-(4-Acetyl-3-hydroxy-2-propylphenoxy)butane thiocyanate

HRID 543231Notes

Reaction equation

HRID 543231 reaction equation
[C:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12]Br)=[C:6]([CH2:16][CH2:17][CH3:18])[C:5]=1[OH:19])(=[O:3])[CH3:2].CS(C)=O.[S-:24][C:25]#[N:26].[K+]>O>[S-:24][C:25]#[N:26].[C:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH3:12])=[C:6]([CH2:16][CH2:17][CH3:18])[C:5]=1[OH:19])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 516872Potassium thiocyanateHCID 133716024-(4-Acetyl-3-hydroxy-2-propylphenoxy)butyl bromide

Product 1

HCID 202058424-(4-Acetyl-3-hydroxy-2-propylphenoxy)butane thiocyanateYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 10.65 g. of 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butyl bromide in 60 ml. of dry dimethylsulfoxide were added 6.5 q. of potassium thiocyanate. The solution was stirred overnight at room temperature and then was poured into water. The solution was extracted twice with dichloromethane. The combined organic extracts were washed with water, dried over magnesium sulfate, filtered, and evaporated in vacuo. The resulting oil was vacuum distilled to provide the title compound in 95% yield as a yellow viscous oil, b.p. about 205° C. at 0.45 torr.

Workup

  1. extractionThe solution was extracted twice with dichloromethane
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. distillationdistilled

Sources & evidence

ORD record
ord-098cecb2bc75454c80342eca97ae3a94
Source dataset
uspto-grants-1987_04
Patent number
US04661505

Reaction notes

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