Toluene → 4-(Cyclopropylcarbonyl)-alpha,alpha-dimethylbenzeneacetonitrile

HRID 348428

Reaktionsgleichung

Reaktionsgleichung von HRID 348428
C1(C(C2C=C[C:9]([CH2:12][C:13]#[N:14])=CC=2)=O)CC1.[CH3:15]I.[O-][CH2:18][CH2:19][CH2:20][CH3:21].[K+].[C:23]1(C)C=CC=C[CH:24]=1.[CH2:30]1[CH2:34][O:33][CH2:32][CH2:31]1>>[CH:30]1([C:34]([C:18]2[CH:24]=[CH:23][C:21]([C:12]([CH3:9])([CH3:15])[C:13]#[N:14])=[CH:20][CH:19]=2)=[O:33])[CH2:31][CH2:32]1

Komponenten

6

Edukt 5

HCID 1140TolueneHCID 6328Methyl iodideHCID 8028Tetrahydrofuran2×HCID 155128314-CyclopropylcarbonylphenylacetonitrileHCID 23699084Potassium butoxide

Produkt 1

HCID 234998454-(Cyclopropylcarbonyl)-alpha,alpha-dimethylbenzeneacetonitrile

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

4-(Cyclopropylcarbonyl)phenylacetonitrile, 15.5 g [JOC, 1973,16, 487] and methyl iodide, 15.5 ml, are dissolved in 75 ml THF. The mixture is cooled to −10° C. and a solution of potassium butoxide (24.5 g) in THF (75 ml) is added so that the temperature of the reaction is kept below 5° C. After 0.5 h more, HPLC shows the reaction to be complete. 200 ml 2M HCI is added followed by 200 ml toluene. The organics are washed with 100 ml 10%. sodium sulphite solution then 100 ml satd sodium chloride solution. The THF is removed and the toluene treated with 5 g silica to remove colour. The toluene is removed and the product crystallises. Yield, 19 g.

Aufarbeitung

  1. customis kept below 5° C
  2. customthe reaction
  3. addition200 ml 2M HCI is added
  4. washThe organics are washed with 100 ml 10%
  5. customThe THF is removed
  6. additionthe toluene treated with 5 g silica
  7. customto remove colour
  8. customThe toluene is removed
  9. customthe product crystallises
  10. customYield

Quellen und Nachweise

ORD-Eintrag
ord-393840dc2e754777826692e274af5201
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176318B2

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