Pyridine → HCID 19911183, compound

HRID 1606245Notes

Reaction equation

HRID 1606245 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:32][C:33](Cl)=[O:34])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>C1C=CC=CC=1>[C:33](=[O:34])([O:32][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[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 108727Decyl chloroformateHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 19911183HCID 19911183, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.384 G. of 4'-cyano-4-hydroxy-biphenyl are dissolved in 3.2 ml. of absolute pyridine and reacted with 0.527 g. of chloroformic acid n-decyl ester as in Example 1. The 0.822 g. of brownish crystals obtained according to the procedure described in Example 1 are dissolved in benzene and chromatographed on 40 g. of silica gel. Benzene elutes 0.714 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-decyl carbonate obtained melts at 59.3°-60.0° and has a clearing point of 74.0°. The compound is smectic in the entire liquid crystalline range. UV (EtOH): ε270 = 26,400.

Workup

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

Sources & evidence

ORD record
ord-c794b71ec51647a0b5da72b074152e06
Source dataset
uspto-grants-1976_04
Patent number
US03952046

Reaction notes

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