Hydrochloric Acid → 2,6-Dichloro-2',3',4'-trimethoxy-6'-methyl-benzophenone

HRID 361966

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:13])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].CCCCCCCC.[Cl:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:24]=1[C:25](Cl)=[O:26].Cl>[Fe](Cl)(Cl)Cl.O.C(OC(=O)C)C>[Cl:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:24]=1[C:25]([C:4]1[C:5]([CH3:13])=[CH:6][C:7]([O:11][CH3:12])=[C:8]([O:9][CH3:10])[C:3]=1[O:2][CH3:1])=[O:26]

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of 3,4,5-trimethoxytoluene (9.11 g; 50 mmol), octane (25 ml) and iron(III)chloride (50 mg) is stirred at 105° C., and percolating nitrogene 2,6-dichlorobenzoylchloride (12.04 g; 57.5 mmol) is added dropwise within 15 minutes. The mixture is kept at 105° C. and stirred for another 15 minutes. After cooling to 50° C. ethylacetate (50 ml) is added, the mixture shaken twice with 2N hydrochloric acid, once with water and dried. The ethylacetate is evaporated (70° C.) and the liquid cooled with stirring. At 50° C. petrolether (50 ml) is added. The white crystals formed are sucked off, washed with petrolether and dried. Yield 12.55 g (70.7%), mp. 92° C.

Workup

additionis added dropwise within 15 minutes
customis kept at 105° C.
stirringstirred for another 15 minutes
additionis added
customdried
customThe ethylacetate is evaporated (70° C.)
temperaturethe liquid cooled
stirringwith stirring
additionAt 50° C. petrolether (50 ml) is added
customThe white crystals formed
washwashed with petrolether
customdried

Sources & evidence

ORD record: ord-6e7b4119066c40779be23be71e686774
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05866722

Linked notes

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