Toluene → HCID 20767651, compound

HRID 372358Notes

Reaction equation

HRID 372358 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].[C-:8]#[N:9].[K+].[C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[C:5]([O:4][CH2:1][C:2]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1)(=[O:7])[CH3:6].[C:1]([O:4][CH2:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:8]#[N:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 7918Acetic AnhydrideHCID 9032Potassium Cyanide

Product 2

HCID 8785Benzyl acetateYield 25%HCID 20767651HCID 20767651, compoundYield 72%

Procedure

A stirred 2-liter autoclave is charged with toluene (400g), cobaltous 2-ethyl hexanoate (2g), acetic anhydride (50g) and potassium cyanide (25g) in that order in the confines of a well ventilated hood. The autoclave is sealed, flushed with N2 and heated to 150° whereupon the N2 pressure of 176 psig is increased to 220 psig with oxygen. The oxygen pressure is maintained at 45 psig during the reaction and at completion of the reaction the product is isolated by distillation. At 1.5% conversion of the toluene there is a 25% yield of benzyl acetate and 72% yield of 2-cyanobenzyl acetate based on the toluene converted.

Workup

  1. customThe autoclave is sealed
  2. customflushed with N2
  3. temperatureheated to 150° whereupon the N2 pressure of 176 psig
  4. temperatureis increased to 220 psig with oxygen
  5. temperatureThe oxygen pressure is maintained at 45 psig during the reaction and at completion of the reaction the product
  6. customis isolated by distillation

Sources & evidence

ORD record
ord-a1dbb46c81804adfb8dbccbefce7c4d1
Source dataset
uspto-grants-1978_05
Patent number
US04091010

Reaction notes

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