Sulfuryl chloride → HCID 13769781, compound

HRID 622909Notes

Reaction equation

HRID 622909 reaction equation
[CH3:1][C:2]([CH3:10])([C:6]([CH3:9])([Cl:8])[CH3:7])[C:3](=[O:5])[CH3:4].S(Cl)([Cl:14])(=O)=O>ClCCl.C1(NC2CCCCC2)CCCCC1>[Cl:14][CH2:4][C:3](=[O:5])[C:2]([CH3:10])([CH3:1])[C:6]([Cl:8])([CH3:9])[CH3:7]

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 13769780HCID 13769780, compound

Product 1

HCID 13769781HCID 13769781, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 7582DicyclohexylamineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

After dissolving 8.0 g of 3,3,4-trimethyl-4-chloro-2-pentanone in 30 ml of dichloromethane, two drops of dicyclohexylamine were added, and then 10.0 g of sulfuryl chloride was added dropwise at 0° C. After addition, the reaction solution was stirred at 20° C for 24 hours, poured into ice water and extracted with dichloromethane. The dichloromethane layer was washed with water, dried over magnesium sulfate and concentrated. The residue obtained was column-chromatographed on silica gel to obtain 6.1 g of 1,4-dichloro-3,3,4-trimethyl-2-pentanone (a compound of the foregoing formula (II) wherein a substituent X is a chlorine atom) as a pale yellow oil.

Workup

  1. additionwere added
  2. additionAfter addition
  3. extractionextracted with dichloromethane
  4. washThe dichloromethane layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue obtained
  8. customwas column-chromatographed on silica gel

Sources & evidence

ORD record
ord-4fc0e44e95fc499f82f5334291c66bc6
Source dataset
uspto-grants-1988_09
Patent number
US04772753

Reaction notes

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