2,6-Dichlorobenzoyl chloride → 2,6-Dichloro-3',4'-dimethoxy-2'-hydroxy-6'-methylbenzophenone

HRID 361965

反応式

HRID 361965 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:7]=1[C:8](Cl)=[O:9].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH3:28])[CH:21]=[C:22]([O:26]C)[C:23]=1[O:24][CH3:25]>ClCCl>[Cl:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:7]=1[C:8]([C:21]1[C:20]([CH3:28])=[CH:19][C:18]([O:17][CH3:16])=[C:23]([O:24][CH3:25])[C:22]=1[OH:26])=[O:9]

参加物

5

反応物 3

HCID 783922,6-Dichlorobenzoyl chlorideHCID 809223,4,5-TrimethoxytolueneHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 185173952,6-Dichloro-3',4'-dimethoxy-2'-hydroxy-6'-methylbenzophenone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

Aluminum chloride (14.67 g, 0.1 mol), 2,6-dichlorobenzoyl chloride (20.95 g, 0.1 mol) and a solution of 3,4,5-trimethoxytoluene (18.22 g, 0.1 mol) in dichloromethane (50 ml), are slowly and consecutively added to dichloromethane stirred at 0° C., stirred for 1 h at ice bath temperatures and for 16 h at room temperature, and poured into ice. The organic layer is separated, washed with dilute hydrochloric acid and water, dried, and, after addition of silica gel (100 g), concentrated in vacuo. A flash chromatography column is packed with silica gel (400 g) andthe charged silica gel is layered on top of that. Elution with petrol ether/ethyl acetate (90/10, 1 l; 80/20, 1 l; 50/50, 1 l) yields 2,6-dichloro-3',4'-dimethoxy-2'-hydroxy-6'-methylbenzophenone, 10.35 g, (30% y), mp. 161° C.

後処理

  1. stirringstirred for 1 h at ice bath temperatures
  2. additionpoured into ice
  3. customThe organic layer is separated
  4. washwashed with dilute hydrochloric acid and water
  5. customdried
  6. additionafter addition of silica gel (100 g)
  7. concentrationconcentrated in vacuo
  8. washElution with petrol ether/ethyl acetate (90/10, 1 l; 80/20, 1 l; 50/50, 1 l)

出典と根拠

ORDレコード
ord-d73ccbad4d6e4cc99abbd33baaaf8750
出典データセット
uspto-grants-1999_02
特許番号
US05866722

関連ノート

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