Dimethyl Sulfoxide → 2-Propenoic acid, 3-cyanopropyl ester

HRID 1779260Notes

Reaction equation

HRID 1779260 reaction equation
CS(C)=O.C(=O)([O-])O.[K+].Br[CH2:11][CH2:12][CH2:13][C:14]#[N:15].[C:16]([OH:20])(=[O:19])[CH:17]=[CH2:18]>CC1(C)N(O)C(C)(C)CC(O)C1.O>[C:16]([O:20][CH2:11][CH2:12][CH2:13][C:14]#[N:15])(=[O:19])[CH:17]=[CH2:18]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6581Acrylic AcidHCID 214124-BromobutyronitrileHCID 516893Potassium Bicarbonate

Product 1

HCID 156854732-Propenoic acid, 3-cyanopropyl esterYield 95.7%

Reagents, catalysts & solvents 2

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a 200 mL three-necked flask, 33 g of dimethyl sulfoxide, 33 g of water, 14.8 g of potassium hydrogencarbonate, 10 g of 4-bromobutyronitrile, and 10 mg of 4-hydroxy TEMPO (4-hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl free radical) were added. Thereafter, 9.8 g of acrylic acid were added thereto dropwise. Then, the contents of the flask were heated to 80° C., and stirred at 80° C. for 4 hours. The resulting reaction liquid was cooled to room temperature. After cooling, the reaction liquid was washed with water, and was purified by column chromatography, to obtain 9 g of 3-cyanopropyl acrylate.

Workup

  1. customThe resulting reaction liquid
  2. temperaturewas cooled to room temperature
  3. temperatureAfter cooling
  4. customthe reaction liquid
  5. washwas washed with water
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-d98060775f8b49058f41db245eaf5f5c
Source dataset
uspto-grants-2016_02
Patent number
US09271401B2

Reaction notes

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