Carbon Dioxide → 3-(3-Hydroxyphenyl)propanenitrile

HRID 1580479Notes

Reaction equation

HRID 1580479 reaction equation
[C:1](=[O:3])=O.[N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11]C=2)[CH:7]=[CH:6][CH:5]=1>>[OH:3][C:1]1[CH:13]=[C:8]([CH2:7][CH2:6][C:5]#[N:4])[CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 280Carbon DioxideHCID 7047Quinoline

Product 1

HCID 17123123-(3-Hydroxyphenyl)propanenitrileYield 69%

Procedure

A 300 ml. flask equipped with a magnetic stirrer, cold water condenser, CO2 outlet and bubbler, and a heated oil bath was charged with 21 g. of crude α-cyano-m-hydroxydihydrocinnamic acid (above) and freshly redistilled quinoline (10 ml.). The acid underwent smooth decarboxylation at an oil bath temperature of 150°C with CO2 evolution ceasing after about 2.5 hr. For workup, the cooled mixture was treated with 200 ml. of 5N HCl and extracted thoroughly with several portions of diethyl ether totalling 350 ml. The ether was washed with water (1 × 100 ml.), saturated NaHCO3 (4 × 50 ml.), brine (1 × 100 ml.), and dried over anhydrous Na2SO4. Concentration of the ether solution gave 11.15 g. (69% yield) of β-(m-hydroxyphenyl)propionitrile as a pale yellow solid. Recrystallization from ethyl acetate/hexane gave the pure compound as light yellow crystals, m.p. 64°-66°C.

Workup

  1. customflask equipped with a magnetic stirrer, cold water condenser, CO2 outlet
  2. additionbubbler, and a heated oil bath was charged with 21 g
  3. customtemperature of 150°C
  4. additionFor workup, the cooled mixture was treated with 200 ml
  5. extractionof 5N HCl and extracted thoroughly with several portions of diethyl ether totalling 350 ml
  6. washThe ether was washed with water (1 × 100 ml.), saturated NaHCO3 (4 × 50 ml.), brine (1 × 100 ml.)
  7. dry with materialdried over anhydrous Na2SO4
  8. customConcentration of the ether solution gave 11.15 g

Sources & evidence

ORD record
ord-7a053b37121e4cf18ba0da6341d9f566
Source dataset
uspto-grants-1976_01
Patent number
US03932678

Reaction notes

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