p-Toluenesulfonic acid → Acetic acid, cyano-, 2-methylpropyl ester

HRID 2226268Notes

Reaction equation

HRID 2226268 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=[O:5])#[N:2].[C:7]1([CH3:17])[CH:12]=CC(S(O)(=O)=O)=C[CH:8]=1>C(O)C(C)C>[C:1]([CH2:3][C:4]([O:6][CH2:8][CH:7]([CH3:17])[CH3:12])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 9740Cyanoacetic acid

Product 1

HCID 25918Acetic acid, cyano-, 2-methylpropyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

495.2 g of 68.7 wt % strength aqueous cyanoacetic acid, 1500 mL of isobutanol and 5 g of p-toluenesulfonic acid were heated to 80° C. in 3 h under a pressure of ca 270 mbar, and the water/isobutanol azeotrope was removed completely. Stirring was then continued for a further 14 h at a ratio of withdrawn to recycled material of 11:99, to give a transition temperature of 67° C. and a final temperature of 88° C. at 200 mbar. Excess isobutanol was distilled off after filtration and 529 g of crude isobutyl cyanoacetate (purity as measured by GC analysis: 90%) were obtained.

Workup

  1. customthe water/isobutanol azeotrope was removed completely
  2. customof withdrawn to recycled material of 11:99
  3. customto give a transition temperature of 67° C.
  4. customtemperature of 88° C.
  5. distillationExcess isobutanol was distilled off
  6. filtrationafter filtration

Sources & evidence

ORD record
ord-627e3c0151134db4a0e0bc0a4e092950
Source dataset
uspto-grants-1994_09
Patent number
US05347032

Reaction notes

Loading…