Pyridine → 4'-Cyano-4-biphenylyl n-octyl carbonate

HRID 1606243Notes

Reaction equation

HRID 1606243 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:30][C:31](Cl)=[O:32])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C1C=CC=CC=1>[C:31](=[O:32])([O:30][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[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 81956Carbonochloridic acid, octyl esterHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 146698384'-Cyano-4-biphenylyl n-octyl carbonate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.390 G. of 4'-cyano-4-hydroxy-biphenyl are dissolved in 10 ml. of absolute pyridine and reacted with 0.423 g. of chloroformic acid n-octyl ester as in Example 1. The 0.721 g. of brownish oil obtained according to the procedure described in Example 1 is dissolved in benzene and chromatographed on 40 g. of silica gel. Benzene elutes 0.620 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-octyl carbonate obtained melts at 51.64° and has a clearing point of 67.7°. UV (EtOH): ε270 = 26,000.

Workup

  1. customof brownish oil 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-618c7b6e221d4441b6059a10a2406d27
Source dataset
uspto-grants-1976_04
Patent number
US03952046

Reaction notes

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