Benzene → HCID 21249991, compound

HRID 1531651Notes

Reaction equation

HRID 1531651 reaction equation
[Cl: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][CH:21]=[CH:20][C:17]=1C=O)([O-:15])=[O:14].[CH:24]1C=CC=CC=1>C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[O:8][CH3:9])[CH:24]([C:21]1[CH:20]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:23][CH:22]=1)[O:12][CH2:11][CH2:10]2

Participants

6

Reactant 3

HCID 241BenzeneHCID 111012-NitrobenzaldehydeHCID 21249988HCID 21249988, compound

Product 1

HCID 21249991HCID 21249991, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Hydrogen chloride gas that is dried for 7 hours is introduced into a suspension of 15.70 g (72.0 mmol) of 2-(3-chloro-4-methoxyphenyl)-ethanol (L. S. Fosdick i.a., J. Am. Chem. Soc. 68 (1946), 840-843), 10.23 g (72.0 mmol) of nitrobenzaldehyde and 9.18 g (72 mmol) of freshly melted zinc chloride in anhydrous benzene (200 ml). Then, the reaction mixture is diluted with ethyl acetate and washed neutral with water, dried and concentrated by evaporation. The residue is recrystallized from ethyl acetate (60 ml). 10.4 g (45%) of 6-chloro-7-methoxy-1-(4-nitrophenyl)-isochroman, melting point 150-153° C., is obtained.

Workup

  1. dry with materialHydrogen chloride gas that is dried for 7 hours
  2. washwashed neutral with water
  3. customdried
  4. concentrationconcentrated by evaporation
  5. customThe residue is recrystallized from ethyl acetate (60 ml)

Sources & evidence

ORD record
ord-67f11d4d119046a990e71cecc313dfe3
Source dataset
uspto-grants-2001_03
Patent number
US06200970B1

Reaction notes

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