Water → 4-Methoxy-3-[6-(4-phenylbut-1-yloxy)hex-1-yloxy]benzaldehyde

HRID 377626ノート

反応式

HRID 377626 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>CN(C)C=O>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[O:1][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12127IsovanillinHCID 110124391-[4-[(6-Bromohexyl)oxy]butyl]benzene

生成物 1

HCID 193562674-Methoxy-3-[6-(4-phenylbut-1-yloxy)hex-1-yloxy]benzaldehyde収率 98.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of 3-hydroxy-4-methoxybenzaldehyde (4.8 grams) in dimethylformamide (100 ml) at room temperature is added potassium carbonate (4.9 grams) and 1-bromo-6-(4-phenylbut-1-yloxy)hexane (10.0 grams). After stirring at 80° C. over 4 hours the reaction mixture is poured into water and extracted with ethyl acetate. The combined organics are washed with 1N sodium hydroxide and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting amber oil is filtered through a 5×10 cm pad of silica gel, eluting with a 1:3 mixture of ethyl acetate and hexane, to give 12.0 grams of a colorless oil. MS (m/z) 384.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organics are washed with 1N sodium hydroxide and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe resulting amber oil is filtered through a 5×10 cm pad of silica gel
  7. washeluting with a 1:3 mixture of ethyl acetate and hexane

出典と根拠

ORDレコード
ord-d9a5e50754914e5992451769dfb68347
出典データセット
uspto-grants-2000_02
特許番号
US06028086

反応ノート

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