Carbon Dioxide → HCID 54010142, compound

HRID 1580480Notes

Reaction equation

HRID 1580480 reaction equation
[C:1]([CH:3]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([OH:16])[CH:9]=1)C(O)=O)#[N:2].N1C2C(=CC=CC=2)C=CC=1.C(=O)=O>>[OH:16][C:10]1[CH:9]=[C:8]([CH2:7][CH2:3][C:1]#[N:2])[CH:13]=[CH:12][C:11]=1[O:14][CH3:15]

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 7047QuinolineHCID 21567094HCID 21567094, compound

Product 1

HCID 54010142HCID 54010142, compoundYield 70%

Conditions

Temperature
165 °C

Procedure

A 100 ml. round bottom flask equipped with a magnetic stirrer, cold water condenser, CO2 outlet and bubbler, and a heated oil bath was charged with 14.9 g. of crude α-cyano-3-hydroxy-4-methoxydihydrocinnamic acid (above) and freshly redistilled quinoline (8 ml.). The acid underwent smooth decarboxylation at an oil bath temperature of 150°-155°C with CO2 evolution continuing 45 min. The mixture was then heated 1 hour at 165°C (oil bath) and permitted to cool to room temperature. For workup, the cooled mixture was treated with 500 ml. of 1N HCl and extracted thoroughly with several portions of ether totalling 350 ml. The ether was washed with water (1 × 100 ml.), saturated NaHCO3 (4 × 50 ml.), brine (1 × 100 ml.), and finally dried over anhydrous Na2SO4. Concentration of the ether solution gave 8.3 g. (70% yield) of β-(3-hydroxy-4-methoxyphenyl)propionitrile as a pale yellow solid. Recrystallization from ethyl acetate/hexane gave the pure compound as light yellow crystals, m.p. 82°C (62% yield of recrystallized product).

Workup

  1. customround bottom flask equipped with a magnetic stirrer, cold water condenser, CO2 outlet
  2. additionbubbler, and a heated oil bath was charged with 14.9 g
  3. customtemperature of 150°-155°C
  4. temperatureto cool to room temperature
  5. additionFor workup, the cooled mixture was treated with 500 ml
  6. extractionof 1N HCl and extracted thoroughly with several portions of ether totalling 350 ml
  7. washThe ether was washed with water (1 × 100 ml.), saturated NaHCO3 (4 × 50 ml.), brine (1 × 100 ml.)
  8. dry with materialfinally dried over anhydrous Na2SO4
  9. customConcentration of the ether solution gave 8.3 g

Sources & evidence

ORD record
ord-0829e3d697d74cf9b0b1baff6a21b9c0
Source dataset
uspto-grants-1976_01
Patent number
US03932678

Reaction notes

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