Water → 6-Bromo-1-[3,4-dimethoxy-5-(1-methylethyl)phenyl]-1-hexanone

HRID 2108262노트

반응식

HRID 2108262 반응식
[CH3:1][CH:2]([C:4]1[C:5]([O:12][CH3:13])=[C:6]([O:10][CH3:11])[CH:7]=[CH:8][CH:9]=1)[CH3:3].[Cl-].[Al+3].[Cl-].[Cl-].[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25].O>C(Cl)Cl>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([C:8]1[CH:9]=[C:4]([CH:2]([CH3:1])[CH3:3])[C:5]([O:12][CH3:13])=[C:6]([O:10][CH3:11])[CH:7]=1)=[O:25]

참가 물질

6

반응물 4

HCID 962WaterHCID 898486-Bromohexanoyl chlorideHCID 51528881-Isopropyl-2,3-dimethoxybenzeneHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 149864006-Bromo-1-[3,4-dimethoxy-5-(1-methylethyl)phenyl]-1-hexanone수율 82%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 5.0 g (0.028 mol) of 3-(1-methylethyl)-1,2-dimethoxybenzene in 5 mL of methylene chloride was added to an ice cooled mixture of 4.4 g (0.033 mol) of aluminum chloride and 7.0 g (0.033 mol) of 6-bromohexanoyl chloride in 50 mL of methylene chloride. The reaction mixture was kept at 0° for 18 hours. Water was added and the organic layer was separated and washed with sodium bicarbonate solution. The dried extract was concentrated under reduced pressure to an oil which was purified by HPLC using 5% ethyl acetate-hexane to give 8.1 g (82% yield) of 6-bromo-1-[3,4-dimethoxy-5-(1-methylethyl)-phenyl]-1-hexanone as an oil. The nmr spectrum was consistent with the structure and the mass spectrum gave the molecular ion at m/z 356 (C17H25BrO3).

후처리

  1. temperaturecooled
  2. customthe organic layer was separated
  3. washwashed with sodium bicarbonate solution
  4. extractionThe dried extract
  5. concentrationwas concentrated under reduced pressure to an oil which
  6. customwas purified by HPLC

출처 및 근거

ORD 기록
ord-f02fe7fc9acb4b4281357e752fd7890f
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04937373

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