Hydrochloric Acid → HCID 21249967, compound

HRID 1531655Notes

Reaction equation

HRID 1531655 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH:11]([OH:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)([O-:16])=[O:15].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[O:8][CH3:9])[CH:21]([C:20]1[CH:23]=[CH:24][C:17]([N+:14]([O-:16])=[O:15])=[CH:18][CH:19]=1)[O:13][CH:11]([CH3:12])[CH2:10]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5414-NitrobenzaldehydeHCID 21249985HCID 21249985, compound

Product 1

HCID 21249967HCID 21249967, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 241BenzeneSolvent

Procedure

A solution of 21.16 g (105.4 mmol) of 1-(3-chloro-4-methoxyphenyl)-2-hydroxypropane in 106 ml of dry benzene is mixed with 15.93 g (105.4 mmol) of 4-nitrobenzaldehyde and 14.36 g (105.4 mmol) of freshly melted zinc chloride, and dry hydrogen chloride gas is introduced for 3 hours. Then, the mixture is heated to boiling for 30 minutes. Working-up is carried out according to the process that is described in Example 3, Step A. The 6-chloro-3-methyl-7-methoxy-1-(4-nitrophenyl)-isochroman that is obtained is first isolated as an oily crude product, which crystallizes during treatment, however, with 370 ml of hot ethanol: 15.79 g (50%, melting point 118-120° C.

Workup

  1. additionis introduced for 3 hours
  2. temperatureThen, the mixture is heated

Sources & evidence

ORD record
ord-e21b97331a9a4b6e820b147f3db8c372
Source dataset
uspto-grants-2001_03
Patent number
US06200970B1

Reaction notes

Loading…