Hydrochloric Acid → 6,7-Dichloro-1-(4-nitrophenyl)-isochromane

HRID 1018452Notes

Reaction equation

HRID 1018452 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[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.[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[Cl:8])[CH:19]([C:18]1[CH:21]=[CH:22][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=1)[O:11][CH2:10][CH2:9]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5414-NitrobenzaldehydeHCID 2445582-(3,4-Dichlorophenyl)ethanol

Product 1

HCID 184015096,7-Dichloro-1-(4-nitrophenyl)-isochromane

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 241BenzeneSolvent

Procedure

19.1 g (100 mM) of 2-(3,4-dichlorophenyl)-ethanol [G. J. Park et al.: J. Org. Chem. 22, 93 (1957)] and 15.1 g (100 mM) of 4-nitrobenzaldehyde were dissolved in 300 ml of anhydrous benzene, then 13.6 g (100 mM) of anhydrous zinc chloride were added and dry hydrochloric acid gas was led into the stirred suspension for 4 hours. Then the process described under Examples 1-7, Step a) was applied. The crude product was recrystallized from ethanol.

Workup

  1. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-0001fb22a4ca4d7985ad80030ff2e66b
Source dataset
uspto-grants-2002_11
Patent number
US06482819B1

Reaction notes

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