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

HRID 965458

反応式

HRID 965458 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
75 °C

実験手順

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 water and 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 of the 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 crystalls are washed with petrolether and sucked off; 0.64 g (39% y), mp. 182° C.

後処理

  1. extractionthe mixture extracted with methylenechloride
  2. washThe extract is washed with water
  3. stirringshaken with 2N sodium hydroxide
  4. dissolutionthe separated compound dissolved in methylenechloride
  5. washthe solution washed with water
  6. customAfter evaporation of the 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 crystalls are washed with petrolether

出典と根拠

ORDレコード
ord-e0902ff2670344b8a8a18cf4659cc88c
出典データセット
uspto-grants-1998_06
特許番号
US05773663

関連ノート

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