3-Hydroxybenzaldehyde → 3-(8-(1,3-Dioxolan-2-yl)octyloxy)benzaldehyde

HRID 332652노트

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HRID 332652 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[O:14][CH2:13][CH2:12][O:11]1.[OH:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[O:11]1[CH2:12][CH2:13][O:14][CH:10]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=[O:20]

참가 물질

6

반응물 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 118323182-(8-Bromooctyl)-1,3-dioxolane

생성물 1

HCID 866768973-(8-(1,3-Dioxolan-2-yl)octyloxy)benzaldehyde수율 80.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a stirred solution of 2-(8-bromooctyl)-1,3-dioxolane (5 g, 18.85 mmol) in dimethyl formamide (100 mL) was added 3-hydroxybenzaldehyde (2.37 g, 19.42 mmol) and potassium carbonate (5.37 g, 38.83 mmol). The reaction mixture was stirred at 80° C. for 16 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution and brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography eluting with 0-100% ethyl acetate in iso-hexane to afford the title compound (4.66 g, 78%).

후처리

  1. extractionextracted with ethyl acetate (×3)
  2. washThe combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution and brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica gel column chromatography
  7. washeluting with 0-100% ethyl acetate in iso-hexane

출처 및 근거

ORD 기록
ord-7ea8671f9a0a407fa9595951e2b5b456
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877774B2

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