Hydrochloric Acid → 4-Oxo-1-phenylcyclohexanenitrile

HRID 76925Notes

Reaction equation

HRID 76925 reaction equation
C(OC([CH:6]1[CH2:11][C:10]([C:18]#[N:19])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][CH2:8][C:7]1=[O:20])=O)C.Cl>C(O)(=O)C.O.[Na+].[Cl-]>[O:20]=[C:7]1[CH2:8][CH2:9][C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)([C:18]#[N:19])[CH2:11][CH2:6]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 690147505-Cyano-2-oxo-5-phenyl-cyclohexane carboxylic acid ethyl ester

Product 1

HCID 912824-Oxo-1-phenylcyclohexanenitrile

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 5234Sodium ChlorideSolvent

Conditions

Temperature
2.5 °C

Procedure

The title compound of step 1 (70.8 g, 261 mmol) in a mixture of acetic acid (810 mL) and concentrated hydrochloric acid (354 mL) was heated to boiling for 3.5 h under DC control. The mixture was then cooled to 0 to 5° C., diluted with water (1 L), saturated with NaCl and extracted cold with ethyl acetate (3×300 mL). The ethyl acetate phase was washed with water and concentrated to low volume in a vacuum. The solid residue was dissolved once again in ethyl acetate, washed with NaHCO3 solution and concentrated until dry.

Workup

  1. temperaturewas heated
  2. extractionextracted cold with ethyl acetate (3×300 mL)
  3. washThe ethyl acetate phase was washed with water
  4. concentrationconcentrated to low volume in a vacuum
  5. dissolutionThe solid residue was dissolved once again in ethyl acetate
  6. washwashed with NaHCO3 solution
  7. concentrationconcentrated
  8. customuntil dry

Sources & evidence

ORD record
ord-93b2a8a0d6fc4c95b319e1292302d4eb
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

Loading…