Isopropanol → Isopropyl cyanoacetate

HRID 650295Notes

Reaction equation

HRID 650295 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=[O:5])#[N:2].[CH:7](O)([CH3:9])[CH3:8].CS(O)(=O)=O>>[C:1]([CH2:3][C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5])#[N:2]

Participants

4

Reactant 3

HCID 3776Isopropanol2×HCID 6395Methanesulfonic AcidHCID 9740Cyanoacetic acid

Product 1

HCID 25917Isopropyl cyanoacetate

Conditions

Temperature
105 °C

Procedure

Cyanoacetic acid (85.5 g; 1.0 mol), isopropanol (80 g; 1.33 mol) and methanesulfonic acid (1.00 g; 0.01 mol) were introduced into a 500 ml flask. The mixture was slowly heated to a maximum of 105° C. while collecting distillates at 77-80° C. Additional isopropanol (220 g; 3.67 mol) was added to maintain the flask at 105-110° C. and the collection of distillates was continued at 77-80° C. After distilling off the unreacted isopropanol, the isopropyl cyanoacetate (bp 100° C./20 mm Hg) was collected as a clear liquid. The yield was 120 g (94.5% of theoretical and its purity was >99% (GC assay).

Workup

  1. distillationwhile collecting distillates at 77-80° C
  2. temperatureto maintain the flask at 105-110° C.
  3. distillationthe collection of distillates
  4. customwas continued at 77-80° C
  5. distillationAfter distilling off the unreacted isopropanol
  6. customthe isopropyl cyanoacetate (bp 100° C./20 mm Hg) was collected as a clear liquid

Sources & evidence

ORD record
ord-484ce8834f104cb98a6fcd769f2d2602
Source dataset
uspto-grants-2001_08
Patent number
US06271410B1

Reaction notes

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