Pyridine → HCID 21404283, compound

HRID 972445Notes

Reaction equation

HRID 972445 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:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>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:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8124Octanoyl chlorideHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 21404283HCID 21404283, 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 0.390 g. of caprylic acid chloride as in Example 1. The 0.671 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 0.586 g. of colorless crytals which are recrystallized from acetone-hexane up to constant melting point and clearing point. The pure 4'-cyano-4-biphenylyl octanoate obtained melts at 77.5°-77.9° and is liquid crystalline (monotrope) upon cooling to 74.1°. UV (EtOH): ε 272 = 26500.

Workup

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

Sources & evidence

ORD record
ord-37e07635b43b48649ae57ec1a9bcfb48
Source dataset
uspto-grants-1977_10
Patent number
US04053431

Reaction notes

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