Hydrochloric Acid → HCID 18401518, compound

HRID 1018453Notes

Reaction equation

HRID 1018453 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([OH:11])[CH3:10])=[CH:4][CH:3]=1.[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)([O-:14])=[O:13].Cl>C1C=CC=CC=1.O.[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:8][CH:9]([CH3:10])[O:11][CH:19]2[C:18]2[CH:21]=[CH:22][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 5414-NitrobenzaldehydeHCID 12499851702-10-3

Product 1

HCID 18401518HCID 18401518, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

11.94 g (70 mM) of 1-(4-chlorophenyl)-2-propanol [J. Med. Chem. 21, 454 (1978)] and 10.57 g (70 mM) of 4-nitrobenzaldehyde were dissolved in 70 ml of anhydrous benzene, then 9.56 g (70 mM) of freshly prepared anhydrous zinc chloride were added and dry hydrochloric acid gas was led into the mixture for 3 hours. Then the mixture was refluxed for 1.5 hours, cooled, diluted with water and the layers were separated. The organic layer was first washed with water then with a solution of sodium hydrogen carbonate, dried and evaporated. The resulting crude product was recrystallized from ethanol.

Workup

  1. temperatureThen the mixture was refluxed for 1.5 hours
  2. temperaturecooled
  3. customthe layers were separated
  4. washThe organic layer was first washed with water
  5. dry with materialwith a solution of sodium hydrogen carbonate, dried
  6. customevaporated
  7. customThe resulting crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-c68388d9ff234052867b24a5190ad74c
Source dataset
uspto-grants-2002_11
Patent number
US06482819B1

Reaction notes

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