Methanesulfonic Acid → HCID 54382959, compound

HRID 650292Notes

Reaction equation

HRID 650292 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=[O:5])#[N:2].[CH2:7]([CH:9]([CH2:12][CH2:13][CH2:14][CH3:15])CO)[CH3:8].[CH3:16]S(O)(=O)=O>>[C:1]([CH2:3][C:4]([O:6][CH:9]([CH2:7][CH3:8])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:5])#[N:2]

Participants

4

Reactant 3

HCID 6395Methanesulfonic AcidHCID 77202-EthylhexanolHCID 9740Cyanoacetic acid

Product 1

HCID 54382959HCID 54382959, compound

Conditions

Temperature
130 °C

Procedure

Cyanoacetic acid (85.5 g; 1.0 mol), 2-ethylhexanol (172 g; 1.32 mol) and methanesulfonic acid (0.47 g; 0.005 mol) were introduced into a 500 ml flask under a nitrogen atmosphere. The reaction vessel was equipped with a distillation column that is provided with means for recycling the alkanol distillate to the flask. The mixture was heated slowly to a maximum of 130° C. while gradually reducing the pressure to about 15 mm of Hg. Water was continuously removed from the distillates (bp 68-80° C./100 mm Hg) and the organic layer (2-ethylhexanol) was returned to the flask until the reaction was complete. After distilling off the unreacted 2-ethylhexanol, the ethylhexyl cyanoacetate (bp 146° C./5 mm Hg) was isolated as a clear liquid. The average yield was 194 g (98.1% of theoretical) having a purity of 99.5% (GC assay).

Workup

  1. customThe reaction vessel was equipped with a distillation column that
  2. customis provided with means
  3. customWater was continuously removed from the distillates (bp 68-80° C./100 mm Hg)
  4. distillationAfter distilling off the unreacted 2-ethylhexanol

Sources & evidence

ORD record
ord-78fbb2a39cdd41ad94a675786d9f7d11
Source dataset
uspto-grants-2001_08
Patent number
US06271410B1

Reaction notes

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