Toluene → (p-Tolylsulphonyl)acetone

HRID 579260

Reaktionsgleichung

Reaktionsgleichung von HRID 579260
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([S:7]([O-:9])=[O:8])=[CH:3][CH:2]=1.[Na+].C1(C)C=CC=CC=1.Cl[CH2:20][C:21](=[O:23])[CH3:22]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:10][C:1]1[CH:6]=[CH:5][C:4]([S:7]([CH2:20][C:21](=[O:23])[CH3:22])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 1140TolueneHCID 6571ChloroacetoneHCID 2723791Sodium p-toluenesulfinate

Produkt 1

HCID 79327(p-Tolylsulphonyl)acetoneAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a 100 ml volume three-necked flask, sodium p-toluenesulfinate (20-a) (9.25 g), tetrabutylammonium bromide (1.65 g), toluene (29 g), and chloroacetone (21-a) (5.0 g) were added, and stirred at 65° C. for 1.25 hours. To the mixture, water (10 g) was added, and stirred for 4 hours. After the mixture was cooled to room temperature, the organic layer was separated, and the aqueous layer was extracted with toluene 2 times. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography (chloroform: ethyl acetate=20:1) to give 9.749 g of 1-(4-methylphenylsulfonyl)-2-propanone (7-2-4).

Aufarbeitung

  1. stirringstirred for 4 hours
  2. temperatureAfter the mixture was cooled to room temperature
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with toluene 2 times
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5d738568e1d94134bc55bf290598a5a9
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040709B2

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