N,N-Dimethylaniline → 4-Methyl-5-phenyl-2H-1,3-dioxol-2-one

HRID 244367Notes

Reaction equation

HRID 244367 reaction equation
O=O.Cl[C:4](Cl)([O:6][C:7](=[O:13])[O:8][C:9](Cl)(Cl)Cl)Cl.CN(C)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.[C:25]1(C)C=CC=CC=1>>[CH3:25][C:4]1[O:6][C:7](=[O:13])[O:8][C:9]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 5

HCID 949N,N-DimethylanilineHCID 962WaterHCID 977OxygenHCID 1140TolueneHCID 94429Triphosgene

Product 1

HCID 128326144-Methyl-5-phenyl-2H-1,3-dioxol-2-one

Procedure

To a solution of the compound of Reference Example 2 (8.5 g) in toluene (75 ml) was added triphosgene (6.4 g), and thereto was added dropwise dimethylaniline (15 g) under ice-cooling, and the mixture was stirred at room temperature for 3 hours. Then, the mixture was further stirred for 4 hours under reflux. After the reaction was completed, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate solution was washed with 1N aqueous hydrochloric acid solution, dried over magnesium sulfate, filtered and concentrated. The obtained residue was purified by column chromatography (hexane:ethyl acetate=4:1) to give the desired product as white crystal (6.16 g).

Workup

  1. temperaturecooling
  2. stirringThen, the mixture was further stirred for 4 hours
  3. temperatureunder reflux
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate solution was washed with 1N aqueous hydrochloric acid solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-46680f05781d46e09b8fc14b666d4750
Source dataset
uspto-grants-2014_02
Patent number
US08658639B2

Reaction notes

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