Benzyl Bromide → 3'-hydroxy4'-benzyloxyacetophenone

HRID 922456

반응식

HRID 922456 반응식
[OH:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C(=O)C>[CH2:18]([O:8][C:7]1[CH:6]=[CH:5][C:4]([C:9](=[O:11])[CH3:10])=[CH:3][C:2]=1[OH:1])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 145303',4'-Dihydroxyacetophenone

생성물 1

HCID 106816283'-hydroxy4'-benzyloxyacetophenone

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

To a solution of 3′,4′-dihydroxyacetophenone (25.4 g) in N,N-dimethylacetamide (420 mL) were added potassium carbonate (23.1 g) and benzyl bromide (19.9 mL) under ice-cooling, and the mixture was stirred at room temperature for 90 minutes. An insoluble was filtered, and then diluted with ethyl acetate. The organic layer was sequentially washed with water and saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane→n-hexane/ethyl acetate=20/1), and then triturated with ethyl acetate to give 1-[4-(benzyloxy)-3-hydroxyphenyl]ethanone [REx(26-1)] (11.0 g) as a colorless powder.

후처리

  1. temperaturecooling
  2. filtrationAn insoluble was filtered
  3. additiondiluted with ethyl acetate
  4. washThe organic layer was sequentially washed with water and saturated saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane→n-hexane/ethyl acetate=20/1)
  8. customtriturated with ethyl acetate

출처 및 근거

ORD 기록
ord-b94a8c71df1443ab85c03bc52a6065f3
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278944B2

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