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

HRID 972451Notes

Reaction equation

HRID 972451 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:29][C:30](Cl)=[O:31])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>C1C=CC=CC=1>[C:30](=[O:31])([O:29][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[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 118547Carbonochloridic acid, heptyl esterHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 214042804'-Cyano-4-biphenylyl n-heptyl carbonate

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 1.07 g. of chloroformic acid n-heptyl ester as in Example 1. The 1.8 g. of yellow oil obtained according to the procedure described in Example 1 is dissolved in benzene and chromatographed on 90 g. of silica gel. Benzene elutes 1.782 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-heptyl carbonate obtained melts at 50.2°-50.5° and has a clearing point of 65.2°. UV (EtOH): ε 270 = 25900.

Workup

  1. customof yellow oil obtained
  2. customchromatographed on 90 g
  3. customof colorless crystals which are recrystallized from ether-hexane up to constant melting point and clearing point

Sources & evidence

ORD record
ord-aa0f6bb6eaa04e078b349408f4bd4cb8
Source dataset
uspto-grants-1977_10
Patent number
US04053431

Reaction notes

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