Acetic Acid → methyl 2-cyano-3-methylbut-2-enoate

HRID 2305822Notes

Reaction equation

HRID 2305822 reaction equation
[CH3:1][C:2]([CH3:4])=O.[C:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])#[N:6].C(O)(=O)C.C([O-])(=O)C.[NH4+]>C1C=CC=CC=1.O>[C:5]([C:7](=[C:2]([CH3:4])[CH3:1])[C:8]([O:10][CH3:11])=[O:9])#[N:6]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 7747Methyl cyanoacetateHCID 517165Ammonium Acetate

Product 1

HCID 248907methyl 2-cyano-3-methylbut-2-enoateYield 58.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

87 g (1.5 mol) of acetone were initially charged in 100 ml of benzene. After addition of 131 g (1.33 mol) of methyl cyanoacetate, 16 g (0.28 mol) of acetic acid and 9.7 g (0.13 mol) of ammonium acetate, the mixture was heated at reflux on a water separator for 10 hours. For work-up, the mixture was washed twice with ¼-concentrated hydrochloric acid and water. The solution was dried with magnesium sulfate and the solvent was removed, and the resulting crude product was distilled. 108 g (55% yield) of methyl 2-cyano-3-methyl-but-2-enoate were isolated (B.p. 95° C./5.2 mbar).

Workup

  1. temperaturethe mixture was heated
  2. washFor work-up, the mixture was washed twice with ¼-concentrated hydrochloric acid and water
  3. dry with materialThe solution was dried with magnesium sulfate
  4. customthe solvent was removed
  5. distillationthe resulting crude product was distilled

Sources & evidence

ORD record
ord-ae9795f43f664da7b6fe6b9e66e97815
Source dataset
uspto-grants-2002_08
Patent number
US06441044B1

Reaction notes

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