Pyridine → HCID 21388873, compound

HRID 1606233Notes

Reaction equation

HRID 1606233 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].N1C=CC=CC=1.[C:22](Cl)(=[O:26])[CH2:23][CH2:24][CH3:25]>C1C=CC=CC=1>[C:22]([O:15][C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)=[CH:10][CH:11]=1)(=[O:26])[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8855Butyryl chlorideHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 21388873HCID 21388873, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.390 G. of 4'-cyano-4-hydroxy-biphenyl are dissolved in 4.0 ml. of absolute pyridine and cooled to -10° with stirring. 0.255 G. of butyric acid chloride are added dropwise thereto over a period of 2 minutes. The temperature rises to 0° and pyridine hydrochloride precipitates out. Subsequently, the mixture is stirred overnight at room temperature and the suspension poured on to a mixture of 12 g. of ice and 12 ml. of 20% hydrochloric acid. Thereafter, this mixture is extracted three times with ethyl acetate, washed with water, dried over sodium sulfate and evaporated in vacuum. The 0.552 g. of yellowish crystals obtained as the residue are dissolved in benzene and chromatographed on 40 g. of silica gel. Benzene elutes 0.521 g. of yellowish crystals which are recrystallized from acetone-hexane up to constant melting point and clearing point. The pure 4'-cyano-4-biphenylyl butyrate obtained melts at 77.9°-78.2° and is liquid crystalline (monotrope) upon cooling to 74.7°. UV (EtOH): ε272 = 26,100.

Workup

  1. customrises to 0°
  2. custompyridine hydrochloride precipitates out
  3. stirringSubsequently, the mixture is stirred overnight at room temperature
  4. additionthe suspension poured on to a mixture of 12 g
  5. extractionThereafter, this mixture is extracted three times with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuum
  9. customof yellowish crystals obtained as the residue
  10. customchromatographed on 40 g
  11. customof yellowish crystals which are recrystallized from acetone-hexane up to constant melting point and clearing point

Sources & evidence

ORD record
ord-f724e72e32e14ad5b59819017cfc5844
Source dataset
uspto-grants-1976_04
Patent number
US03952046

Reaction notes

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