Diethyl Carbonate → Ethyl cyano(3,4-dimethoxyphenyl)acetate

HRID 1464149Notes

Reaction equation

HRID 1464149 reaction equation
[Na].[C:2](#[N:14])[CH2:3][C:4]1[CH:13]=[CH:12][C:9]([O:10][CH3:11])=[C:6]([O:7][CH3:8])[CH:5]=1.[C:15](=O)([O:19]CC)[O:16][CH2:17][CH3:18]>>[CH3:8][O:7][C:6]1[CH:5]=[C:4]([CH:3]([C:2]#[N:14])[C:15]([O:16][CH2:17][CH3:18])=[O:19])[CH:13]=[CH:12][C:9]=1[O:10][CH3:11]

Participants

4

Reactant 3

HCID 7766Diethyl CarbonateHCID 667273,4-DimethoxybenzeneacetonitrileHCID 5360545Sodium

Product 1

HCID 12814070Ethyl cyano(3,4-dimethoxyphenyl)acetate

Procedure

25.7 g (1.1 mol eq.) of sodium in small pieces were added gradually to a solution of 198 g (1.1 mol) of homoveratronitrile in 500 ml of diethyl carbonate in such a manner that the temperature remained at approximately 100°. Thereafter, the reaction mixture was heated to reflux for 1 hour, evaporated under reduced pressure, treated with cooled water, acidified with 70 ml of glacial acetic acid and extracted with ether. The combined organic extracts were dried and evaporated. The residual oil was distilled in a high vacuum, whereby ethyl 3,4-dimethoxyphenylcyanoacetate was obtained, b.p. 170°-172°/70 Pa. HPLC purity >99%.

Workup

  1. customremained at approximately 100°
  2. temperatureThereafter, the reaction mixture was heated
  3. temperatureto reflux for 1 hour
  4. customevaporated under reduced pressure
  5. additiontreated with cooled water
  6. extractionextracted with ether
  7. customThe combined organic extracts were dried
  8. customevaporated
  9. distillationThe residual oil was distilled in a high vacuum

Sources & evidence

ORD record
ord-8c7fb1d8e9df4f73a3106f56b95f2adc
Source dataset
uspto-grants-1994_04
Patent number
US05302727

Reaction notes

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