Water → 5-Chloro-2,2-dimethyl-1,3-dioxin-4-one

HRID 226222Notes

Reaction equation

HRID 226222 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH3:6][C:7]1([CH3:14])[O:12][C:11](=[O:13])[CH:10]=[CH:9][O:8]1.O>N1C=CC=CC=1>[Cl:4][C:10]1[C:11](=[O:13])[O:12][C:7]([CH3:14])([CH3:6])[O:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 131570352,2-Dimethyl-2,4-dihydro-1,3-dioxin-4-one

Product 1

HCID 666017795-Chloro-2,2-dimethyl-1,3-dioxin-4-oneYield 51.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Sulfuryl chloride (2.44 mL, 0.03 mol) was added dropwise to a solution of 2,2-dimethyl-1,3-dioxin-4-one (3.2 g, 0.025 mol) in pyridine (16 mL) under cooling with ice. The mixture was stirred for 30 minutes, while the temperature was maintained, and was further stirred at room temperature for two hours. The reaction mixture was cooled with ice, and water was added to the reaction mixture. The reaction mixture was extracted with dichloromethane, and the formed dichloromethane layer was dried over sodium sulfate anhydrate and concentrated. The concentration residue was purified through silica gel column chromatography (eluent=n-hexane:ethyl acetate=95:5), to thereby yield 2.08 g of the title compound as an oily substance (yield: 51.2%).

Workup

  1. temperatureunder cooling with ice
  2. temperaturewas maintained
  3. stirringwas further stirred at room temperature for two hours
  4. additionwas added to the reaction mixture
  5. extractionThe reaction mixture was extracted with dichloromethane
  6. dry with materialthe formed dichloromethane layer was dried over sodium sulfate anhydrate
  7. concentrationconcentrated
  8. customThe concentration residue was purified through silica gel column chromatography (eluent=n-hexane:ethyl acetate=95:5)

Sources & evidence

ORD record
ord-b87eb878afd349bdae9fb08b721c6e3e
Source dataset
uspto-grants-2009_07
Patent number
US07557216B2

Reaction notes

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