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

HRID 732941

Reaction equation

HRID 732941 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A stirred slurry of toluene-4-sulfonic acid cyanomethyl ester (13.0 g), potassium carbonate (13.0 g) and 2-isopropyl-4-methoxyphenol (9.57 g) in 85 mL of 2-butanone was heated to 55-60 degrees C. for 4 days, then heated to reflux 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 under reduced pressure 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 aliquot (0.967 g) of this solution was concentrated to dryness to give 0.509 g of crude (2-Isopropyl-4-methoxy-phenoxy)-acetonitrile, MS (M+H)=206.

Workup

  1. temperatureheated
  2. temperatureto reflux 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 under reduced pressure

Sources & evidence

ORD record
ord-01884a54a50d4c16a02f82ea43c6704d
Source dataset
uspto-grants-2009_09
Patent number
US07589090B2

Linked notes

Loading…