Hydrochloric Acid → HCID 10591888, compound

HRID 1742876Notes

Reaction equation

HRID 1742876 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23].Cl>CCCCC>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([C:19]1[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[C:17]([O:22][CH3:23])[CH:18]=1)=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7043VeratroleHCID 117637Benzoyl chloride, 2-chloro-5-nitro-

Product 1

HCID 10591888HCID 10591888, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
150 °C

Procedure

2-Chloro-5-nitrobenzoyl chloride (11 g; 0.05 mole), 1,2-dimethoxybenzene (20 ml; 0.15 mole) and anhydrous ferric chloride (0.5 g) are successively introduced into a flask. The mixture is progressively heated to 150° C., and maintained at this temperature for 1 hour. After cooling, the reaction mixture is poured into 1N HCl (200 ml), then extracted with dichloromethane (3×200 ml). After washing with a sodium bicarbonate solution, the organic phase is dried over MgSO4 and then concentrated under reduced pressure to provide a brown oil. By trituration with pentane (300 ml), 2-chloro-3',4'-dimethoxy-5-nitrobenzophenone (12.5 g; yield: 78%) is isolated in the form of a beige solid of m.p. 138° C. (compound no. 171).

Workup

  1. temperaturemaintained at this temperature for 1 hour
  2. temperatureAfter cooling
  3. extractionextracted with dichloromethane (3×200 ml)
  4. washAfter washing with a sodium bicarbonate solution
  5. dry with materialthe organic phase is dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customto provide a brown oil

Sources & evidence

ORD record
ord-f6576afe7ace48f5b3c6ca8be2b5d9ab
Source dataset
uspto-grants-1994_08
Patent number
US05342835

Reaction notes

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