Acetic Acid → 4-Cyclohexylcyclohexylidenephosphorohydrazidic Acid, Diethyl Ester

HRID 1614463

Reaction equation

HRID 1614463 reaction equation
[CH:1]1([CH:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(=O)C.[P:18]([NH:26][NH2:27])(=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]>C(Cl)Cl>[CH:1]1([CH:7]2[CH2:12][CH2:11][C:10](=[N:27][NH:26][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 41690(1,1'-Bicyclohexyl)-4-oneHCID 143340Phosphorohydrazidic acid, diethyl ester

Product 1

HCID 855407454-Cyclohexylcyclohexylidenephosphorohydrazidic Acid, Diethyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-cyclohexylcyclohexanone (27.04 g) and acetic acid (3 ml) in CH2Cl2 (400 ml) was added a solution of diethyl phosphorohydrazidate (28.91 g) in CH2Cl2 (100 ml). The reaction was stirred at room temperature for 27 hours and then was concentrated under reduced pressure. Toluene was added (2×) and removed under reduced pressure in order to aid in the removal of acetic acid by co-distillation. The residual yellow liquid was the product and was used without further purification. TLC Rf=0.52 (20% acetone in CH2Cl2, silica gel).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionToluene was added (2×)
  3. customremoved under reduced pressure in order
  4. customto aid in the removal of acetic acid by co-distillation
  5. customwas used without further purification

Sources & evidence

ORD record
ord-cdb1b8a10ee54fd08606c2a81d50cb77
Source dataset
uspto-grants-1993_03
Patent number
US05196542

Linked notes

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