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

HRID 2040743Notes

Reaction equation

HRID 2040743 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 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 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 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. An aliquot (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)

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 by distillation

Sources & evidence

ORD record
ord-9ccfd55c439f43d2ba0962cbb24fd06c
Source dataset
uspto-grants-2013_11
Patent number
US08580960B2

Reaction notes

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