1-Propanol → Propyl cyanoacetate

HRID 650294Notes

Reaction equation

HRID 650294 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=[O:5])#[N:2].[CH2:7](O)[CH2:8][CH3:9].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:1]([CH2:3][C:4]([O:6][CH2:7][CH2:8][CH3:9])=[O:5])#[N:2]

Participants

4

Reactant 3

HCID 10311-PropanolHCID 9740Cyanoacetic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 84444Propyl cyanoacetate

Conditions

Temperature
105 °C

Procedure

Cyanoacetic acid (85.5 g; 1.0 mol), 1-propanol (120 g; 2.0 mol) and p-toluenesulfonic acid monohydrate (1.00 g; 0.005 mol) were introduced into a 500 ml flask. The mixture was slowly heated to a maximum of 105° C. while collecting distillates at 88-90° C. The pressure was reduced so that the flask was maintained at 105-110° C. and the distillates were collected continuously, and the propanol was returned to the flask. After distilling off the unreacted propanol, the n-propyl cyanoacetate (bp 100° C./23 mm Hg) was collected as a clear liquid. The yield was 122 g (96% of theoretical) and its purity was >99% (GC assay).

Workup

  1. distillationwhile collecting distillates at 88-90° C
  2. temperaturewas maintained at 105-110° C.
  3. distillationthe distillates were collected continuously
  4. distillationAfter distilling off the unreacted propanol
  5. customthe n-propyl cyanoacetate (bp 100° C./23 mm Hg) was collected as a clear liquid

Sources & evidence

ORD record
ord-b87158ba3ac34bf1ae423aa4b9981c17
Source dataset
uspto-grants-2001_08
Patent number
US06271410B1

Reaction notes

Loading…