Sulfuric Acid → Prop-2-yn-1-yl cyanoacetate

HRID 1613685Notes

Reaction equation

HRID 1613685 reaction equation
[CH2:1](O)[C:2]#[CH:3].[C:5]([CH2:7][C:8]([OH:10])=[O:9])#[N:6].S(=O)(=O)(O)O>C(Cl)(Cl)Cl>[C:5]([CH2:7][C:8]([O:10][CH2:3][C:2]#[CH:1])=[O:9])#[N:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7859Propargyl alcoholHCID 9740Cyanoacetic acid

Product 1

HCID 14972819Prop-2-yn-1-yl cyanoacetateYield 71%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.6 parts of propargyl alcohol and 1 part of cyanoacetic acid were dissolved in 4.7 parts of chloroform. 0.2 parts of a 98 percent by weight solution of aqueous sulfuric acid were added as a catalyst and the resultant mixture was heated for 5.5 hours at a temperature of 61° C. The crude ester was washed with water. Volatile materials were removed using reduced pressure. The ester, represented the formula N≡CCH2C(O)OCH2C≡CH, was isolated in 71 percent yield.

Workup

  1. washThe crude ester was washed with water
  2. customVolatile materials were removed
  3. customwas isolated in 71 percent yield

Sources & evidence

ORD record
ord-271dc5cac8244e3a8d26127bcd1f1d1c
Source dataset
uspto-grants-1993_03
Patent number
US05194460

Reaction notes

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