Sulfuryl chloride → HCID 20472519, compound

HRID 2296366Notes

Reaction equation

HRID 2296366 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9](=[O:20])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(C1C=CC=CC=1)(=O)CCCCCCCCCC.S(Cl)([Cl:42])(=O)=O>C(Cl)(Cl)Cl>[Cl:42][C:5]1[C:4]([OH:8])=[C:3]([C:9](=[O:20])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:2]([OH:1])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 781671-PhenylundecanoneHCID 204320541-(2,6-Dihydroxyphenyl)undecan-1-one

Product 1

HCID 20472519HCID 20472519, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

In a 100 ml three-neck flask was placed 50 ml of 2',6'-dihydroxyundecanophenone and after dissolving the undecanophenone in 50 ml of chloroform, the solution thus formed was stirred under ice-cooling. To the solution was added dropwise 10 ml of a chloroform solution of 1.4 ml of sulfuryl chloride over a period of 15 minutes. Thereafter, the mixture was stirred for 2 hours at room temperature and then after adding thereto n-hexane, the mixture was washed twice with water. After drying the reaction mixture with magnesium sulfate, the product was concentrated and the residue thus obtained was recrystallized from methanol to provide the light yellow crystals of 3'-chloro-2',6'-dihydroxyundecanophenone having a melting point of 76°-77° C. The structure was confirmed by carrying out analysis such as mass spectrography and nuclear magnetic resonance spectra.

Workup

  1. customIn a 100 ml three-neck flask was placed
  2. customthe solution thus formed
  3. temperaturecooling
  4. stirringThereafter, the mixture was stirred for 2 hours at room temperature
  5. additionafter adding
  6. washn-hexane, the mixture was washed twice with water
  7. dry with materialAfter drying the reaction mixture with magnesium sulfate
  8. concentrationthe product was concentrated
  9. customthe residue thus obtained
  10. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-02fb6437637f4beda89b97c8ebb95df5
Source dataset
uspto-grants-1984_01
Patent number
US04429035

Reaction notes

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