Acetic Acid → Ethyl 2-cyano-3-ethylpent-2-enoate

HRID 359491Notes

Reaction equation

HRID 359491 reaction equation
[CH3:1][CH2:2][C:3](=O)[CH2:4][CH3:5].[C:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:8].C(O)(=O)C.C([O-])(=O)C.[NH4+]>C1(C)C=CC=CC=1>[C:7]([C:9](=[C:3]([CH2:4][CH3:5])[CH2:2][CH3:1])[C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7288Ethyl ketoneHCID 7764Ethyl cyanoacetateHCID 517165Ammonium Acetate

Product 1

HCID 349978Ethyl 2-cyano-3-ethylpent-2-enoateYield 50.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 473 g (5.5 mol) of 3-pentanone, 565 g (5 mol) of ethyl cyanoacetate, 60 g (1 mol) of acetic acid, 38.5 g (0.5 mol) of ammonium acetate and 500 ml of toluene was stirred and heated under a Dean-Stark trap for 7 hr. and then allowed to stand for 2 days at room temperature. The reaction mixture was washed three times with 1 l of water and concentrated on the rotary evaporator at a low temperature. The residue was distilled in vacuum to give 460 g of ethyl 2-cyano-3,3-diethylacrylate, bp 118°-120°/8 mm.

Workup

  1. temperatureheated under a Dean-Stark trap for 7 hr
  2. washThe reaction mixture was washed three times with 1 l of water
  3. concentrationconcentrated on the rotary evaporator at a low temperature
  4. distillationThe residue was distilled in vacuum

Sources & evidence

ORD record
ord-53b0269be3404d7396126928cde6bd83
Source dataset
uspto-grants-1991_03
Patent number
US05001140

Reaction notes

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