Hydrochloric Acid → 2,3-Dichloro-2',4-dimethoxybenzophenone

HRID 568685Notes

Reaction equation

HRID 568685 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:7]=1[O:13][CH3:14].[CH3:15][O:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20].Cl>ClCCCl.CCCCCC>[Cl:12][C:11]1[C:6]([Cl:5])=[C:7]([O:13][CH3:14])[CH:8]=[CH:9][C:10]=1[C:19]([C:18]1[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=1[O:16][CH3:15])=[O:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 161262,3-DichloroanisoleHCID 889692-Methoxybenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 140125702,3-Dichloro-2',4-dimethoxybenzophenone

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8058HexaneSolvent

Conditions

Temperature
5 °C

Procedure

To a mixture of 3.9 g of AlCl3 and 4.67 g of 2,3-dichloroanisole in 70 ml of 1,2-dichloroethane at -10° C., 5 g of o-methoxybenzoyl chloride is added dropwise. The mixture is stirred for 2.5 hours and is gradually warmed to 5° C. The reaction mixture is poured into concentrated HCl and ice. The mixture is stirred one half hour to decompose the complex. The aqueous layer is extracted with additional organic solvent. The combined organic layers are washed until neutral, dried over Na2SO4 and evaporated to give an oil which solidifies on trituration with hexane. The crude product is recrystallized from 95% ethanol giving 2,3-dichloro-2',4-dimethoxybenzophenone, mp 94°-96° C.

Workup

  1. stirringThe mixture is stirred one half hour
  2. extractionThe aqueous layer is extracted with additional organic solvent
  3. washThe combined organic layers are washed until neutral,
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customto give an oil which
  7. customThe crude product is recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-985b2a55c6124d4481bb00b4b45d92e2
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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