Acetic Acid → 2,6-Dichloro-2',3'-dihydroxy-4'-methoxy-6'-methyl-benzophenone

HRID 361967

Reaktionsgleichung

Reaktionsgleichung von HRID 361967
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([O:13][CH3:14])=[C:8]([O:15]C)[C:7]=1[O:17]C)=[O:5].Br.C(O)(=O)C>O>[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([O:13][CH3:14])=[C:8]([OH:15])[C:7]=1[OH:17])=[O:5]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 227199532,6-Dichloro-2',3',4'-trimethoxy-6'-methyl-benzophenone

Produkt 1

HCID 545695512,6-Dichloro-2',3'-dihydroxy-4'-methoxy-6'-methyl-benzophenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of 2,6-dichloro-2',3',4'-trimethoxy-6'-methyl-benzophenone (1.78 g; 5 mmol) hydrobromic acid (7.5 ml; 30% in acetic acid) and acetic acid (7.5 ml) is stirred at 75° C. for 2 hours. Water is added and the mixture extracted with methylenechloride. The extract is washed with waterand shaken with 2N sodium hydroxide. The alcaline solution is acidified with hydrochloric acid, the separated compound dissolved in methylenechloride and the solution washed with water. After evaporation ofthe solvent purification is carried out by chromatography (flash column, filled with 36 g of silicagel; elution with 500 ml of petrolether/ethylacetate (4:1; v/v) and 250 ml of petrolether/ethylacetate(1:1; v/v)). the fraction containing the compound is concentrated, the compound crystallized. The yellow crystals are washed with petrolether andsucked off; 0.64 g (39% y), mp. 182° C.

Aufarbeitung

  1. extractionthe mixture extracted with methylenechloride
  2. washThe extract is washed with waterand
  3. stirringshaken with 2N sodium hydroxide
  4. dissolutionthe separated compound dissolved in methylenechloride
  5. washthe solution washed with water
  6. customAfter evaporation ofthe solvent purification
  7. additionis carried out by chromatography (flash column, filled with 36 g of silicagel; elution with 500 ml of petrolether/ethylacetate (4:1; v/v) and 250 ml of petrolether/ethylacetate(1:1; v/v))
  8. additionthe fraction containing the compound
  9. concentrationis concentrated
  10. customthe compound crystallized
  11. washThe yellow crystals are washed with petrolether

Quellen und Nachweise

ORD-Eintrag
ord-f2bc4d1e56aa4859abea606d965acb6e
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866722

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