Pyridine → HCID 21404285, compound

HRID 1606241Notes

Reaction equation

HRID 1606241 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.[CH2:22]([O:28][C:29](Cl)=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C1C=CC=CC=1>[C:29](=[O:30])([O:28][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[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

Participants

5

Reactant 3

HCID 1049PyridineHCID 22466Hexyl chloroformateHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 21404285HCID 21404285, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.976 G. of 4'-cyano-4-hydroxy-biphenyl are dissolved in 10 ml. of absolute pyridine and reacted with 0.988 g. of chloroformic acid n-hexyl ester as in Example 1. The 1.675 g. of yellowish, turbid, partially crystallized oil obtained according to the procedure described in Example 1 is dissolved in benzene and chromatographed on 80 g. of silica gel. Benzene elutes 1.530 g. of colorless crystals which are recrystallized from ether-hexane up to constant melting point and clearing point. The pure 4'-cyano-4-biphenylyl n-hexyl carbonate obtained melts at 87.1°-87.5° and is liquid crystalline (monotrope) upon cooling to 62.7°. UV (EtOH): ε270 = 26,300.

Workup

  1. customof yellowish, turbid, partially crystallized oil obtained
  2. customchromatographed on 80 g
  3. customof colorless crystals which are recrystallized from ether-hexane up to constant melting point and clearing point

Sources & evidence

ORD record
ord-9cfe8c40998341cbbbe2ea5854af5269
Source dataset
uspto-grants-1976_04
Patent number
US03952046

Reaction notes

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