Butyl chloroformate → HCID 21404282, compound

HRID 1606239Notes

Reaction equation

HRID 1606239 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].[CH2:16]([O:20][C:21](Cl)=[O:22])[CH2:17][CH2:18][CH3:19]>N1C=CC=CC=1>[C:21](=[O:22])([O:20][CH2:16][CH2:17][CH2:18][CH3:19])[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

4

Reactant 2

HCID 61140Butyl chloroformateHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 21404282HCID 21404282, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.390 G. of 4'-cyano-4-hydroxy-biphenyl are dissolved in 4.0 ml. of absolute pyridine and reacted 0.328 g. of chloroformic acid n-butyl ester as in Example 1. The 0.579 g. of colorless oil obtained according to the procedure described in Example 1 crystallizes after trituration. The crystals are dissolved in benzene and chromatographed on 40 g. of silica gel. Benzene elutes 0.521 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-butyl carbonate obtained melts at 64.8°-65.7° and is liquid crystalline (monotrope) upon cooling to 64.3°. UV (EtOH): ε270 = 26,300.

Workup

  1. customof colorless oil obtained
  2. customcrystallizes after trituration
  3. dissolutionThe crystals are dissolved in benzene
  4. customchromatographed on 40 g
  5. customof colorless crystals which are recrystallized from ether/hexane up to constant melting point and clearing point

Sources & evidence

ORD record
ord-fb724df923cd4e12a66975e75346f854
Source dataset
uspto-grants-1976_04
Patent number
US03952046

Reaction notes

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