Potassium Carbonate → 2-(4-Methoxy-2-propan-2-ylphenoxy)acetonitrile

HRID 18668

Reaktionsgleichung

Reaktionsgleichung von HRID 18668
[C:1]([CH2:3]OS(C1C=CC(C)=CC=1)(=O)=O)#[N:2].C(=O)([O-])[O-].[K+].[K+].[CH:21]([C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=1[OH:32])([CH3:23])[CH3:22]>CC(=O)CC>[CH:21]([C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=1[O:32][CH2:3][C:1]#[N:2])([CH3:23])[CH3:22]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 84525Acetonitrile, 2-(((4-methylphenyl)sulfonyl)oxy)-HCID 183649974-Methoxy-2-(propan-2-yl)phenol

Produkt 1

HCID 252417712-(4-Methoxy-2-propan-2-ylphenoxy)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A stirred slurry of toluene-4-sulfonic acid cyanomethyl ester (13.0 kg), potassium carbonate (13.0 kg) and 2-isopropyl-4-methoxyphenol (9.57 Kg) in 79.7 kg of 2-butanone was heated to 55-60 degrees C. for 4 days, then heated to relux for 18 hours. The resultant slurry was cooled and filtered to remove solids. The filtrate was concentrated under reduced pressure and the residue was redissolved in toluene. The toluene solution was extracted with 1N KOH, and the organic phase was concentrated by distillation to give 20.6 g of a 1:1 (by weight) solution of (2-Isopropyl-4-methoxy-phenoxy)-acetonitrile in toluene, which was used directly in the next step. A anliquot (96.7 g) of this solution was concentrated to dryness to give 50.9 g of crude (2-Isopropyl-4-methoxy-phenoxy)-acetonitrile, projecting to a yield of 10.9 kg in the bulk solution: MS (M+H)=206; 1H nmr (CDCl3) delta: 1.25 (d, J=6.9 Hz), 3.31 (septet, 1H, J=6.9 Hz), 3.82 (s, 3H), 4.76 (s, 2H), 6.73 (dd. 1H, J=8.8 Hz, 3.1 Hz), 6.87 (d, 1H, J=3.1 Hz), 6.91 (d, 1H, J=8.8 Hz)

Aufarbeitung

  1. temperatureheated
  2. waitto relux for 18 hours
  3. temperatureThe resultant slurry was cooled
  4. filtrationfiltered
  5. customto remove solids
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. dissolutionthe residue was redissolved in toluene
  8. extractionThe toluene solution was extracted with 1N KOH
  9. concentrationthe organic phase was concentrated by distillation

Quellen und Nachweise

ORD-Eintrag
ord-cf9b8be9f1a34379a13bab8f30306493
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741484B2

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