Pyridine → HCID 13741932, compound

HRID 1606237Notes

Reaction equation

HRID 1606237 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:31])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>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:31])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 1049PyridineHCID 69819Nonanoyl chlorideHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 13741932HCID 13741932, 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 0.424 g. of pelargonic acid chloride as in Example 1. The 0.722 g. of yellow crystals obtained according to the procedure described in Example 1 are dissolved in benzene and chromatographed on 40 g. of silica gel. Benzene elutes 0.617 g. of colorless crystals which are recrystallized from acetone-hexane up to constant melting point and clearing point. The pure 4'-cyano-4-biphenylyl nonanoate obtained melts at 43.2°-43.6° and has a clearing point of 74.0°. The compound is smectic up to 61.3°. UV (EtOH): ε272 = 26,900.

Workup

  1. customof yellow 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-293b52fa889147379e4c8a0c63363590
Source dataset
uspto-grants-1976_04
Patent number
US03952046

Reaction notes

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