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

HRID 377626노트

반응식

HRID 377626 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d9a5e50754914e5992451769dfb68347
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06028086

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