Pyridine → HCID 4134902, compound

HRID 972444Notes

Reaction equation

HRID 972444 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:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>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:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67340Hexanoyl chlorideHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 4134902HCID 4134902, 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 reacted with 0.323 g. of caproic acid chloride as in Example 1. The 0.613 g. of yellowish crystals obtained according to the procedure described in Example 1 are dissolved in benzene and chromatographed on 40 g. of silica gel. Benzene elutes 0.555 g. of colorless crystals which are recrystallized from acetone-hexane up to constant melting point and clearing point. The pure 4'-cyano-4-biphenylyl hexanoate obtained melts at 56.1° and has a clearing point of 70.7° UV (EtOH): ε 273 = 26400.

Workup

  1. customof yellowish crystals obtained
  2. customchromatographed on 40 g
  3. customof colorless crystals which are recrystallized from acetone-hexane up to constant melting point and clearing point

Sources & evidence

ORD record
ord-a789ceec8c294535b924da3a8530dae3
Source dataset
uspto-grants-1977_10
Patent number
US04053431

Reaction notes

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