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

HRID 361965

반응식

HRID 361965 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d73ccbad4d6e4cc99abbd33baaaf8750
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866722

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