Hydrochloric Acid → 2,6-Dichloro-4'-hydroxy-5'-nitro-2'-methyl-benzophenone

HRID 361972

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:7]=1[C:8]([C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[C:13]([O:19]C)=[CH:12][C:11]=1[CH3:21])=[O:9].Cl.O>C(Cl)Cl>[Cl:5][C:6]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:7]=1[C:8]([C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[C:13]([OH:19])=[CH:12][C:11]=1[CH3:21])=[O:9]

Participants

Conditions

Temperature: 45 °C

Procedure

Aluminumchloride (1.5 g; 11 mmol) is added to a solution of 2,6-dichloro-5'-nitro-4'-methoxy-2'-methyl-benzophenone (1.8 g; 5.3 mmol) in methylenechloride (6 ml). The mixture is stirred for 30 minutes at 20° C. and for 1 hour at 45° C., 5 ml conc. hydrochloric acid/ice are added. After shaking with 20 ml of methylenechloride the organic layer is treated with 2N hydrochloric acid and with water. After drying the solvent is evaporated, the residue purified by chromatography (flash column filled with 30 g of silicagel, elution with toluene). The residue from the main fraction is treated with diisopropylether to give yellow crystals; (1.2 g; 73% y); mp. 170° C.

Workup

customAfter drying the solvent
customis evaporated
customthe residue purified by chromatography (flash column filled with 30 g of silicagel, elution with toluene)
additionThe residue from the main fraction is treated with diisopropylether
customto give yellow crystals

Sources & evidence

ORD record: ord-643488945a8f40ec9c390d4bf5e49093
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05866722

Linked notes

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