4-Nitrobenzaldehyde → HCID 21249966, compound

HRID 1531650Notes

Reaction equation

HRID 1531650 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)([O-:15])=[O:14]>C1C=CC=CC=1.C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-]>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[O:8][CH3:9])[CH:20]([C:19]1[CH:22]=[CH:23][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=1)[O:12][CH2:11][CH2:10]2

Participants

6

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 230022542-(3-bromo-4-methoxyphenyl)ethanol

Product 1

HCID 21249966HCID 21249966, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Hydrogen chloride gas that is dried for 5 hours is introduced into a suspension of 7.50 g (32.4 mmol) of 2-(3-bromo-4-methoxy-phenyl)-ethanol, 4.90 g (32.4 mmol) of 4-nitro-benzaldehyde and 4.39 g (32.4 mmol) of freshly melted zinc chloride in anhydrous benzene (96 ml). The reaction mixture is then diluted with ethyl acetate and washed neutral with water. After drying and concentration by evaporation, the solid residue is recrystallized from ethyl acetate (25 ml). 7.91 g (67%) of 6-bromo-7-methoxy-l-(4-nitrophenyl)-isochroman, melting point 144-147° C., is obtained.

Workup

  1. dry with materialHydrogen chloride gas that is dried for 5 hours
  2. washwashed neutral with water
  3. customAfter drying
  4. concentrationconcentration
  5. customby evaporation
  6. customthe solid residue is recrystallized from ethyl acetate (25 ml)

Sources & evidence

ORD record
ord-2b89ce5f6ae94ad0a10ec36c02ddb558
Source dataset
uspto-grants-2001_03
Patent number
US06200970B1

Reaction notes

Loading…