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

HRID 332652ノート

反応式

HRID 332652 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-7ea8671f9a0a407fa9595951e2b5b456
出典データセット
uspto-grants-2014_11
特許番号
US08877774B2

反応ノート

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