Water → 3-Iodo-5-methoxy-4-propoxybenzaldehyde

HRID 1708448

반응식

HRID 1708448 반응식
[I:1][C:2]1[C:3]([OH:12])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH2:19](I)[CH2:20][CH3:21].O>CN(C=O)C>[CH3:11][O:10][C:4]1[CH:5]=[C:6]([CH:9]=[C:2]([I:1])[C:3]=1[O:12][CH2:19][CH2:20][CH3:21])[CH:7]=[O:8]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 79499Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-

생성물 1

HCID 47701013-Iodo-5-methoxy-4-propoxybenzaldehyde수율 93.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5-Iodovanillin (25 g, 0.09 mol) in DMF (100 mL) was treated with potassium carbonate (32 g, 0.23 mol) and n-propyl iodide (52 g. 0.3 mol, 31 mL) and heated for 16 hours. The solution was allowed to cool to room temperature and then poured into water (500 mL) and extracted with ether (3×250 mL). The organic layers were combined and washed with water and saturated sodium chloride solution, and then dried over magnesium sulfate. The organic layer was evaporated by distillation under diminished pressure to an oil, and then purified by column chromatography (silica, 7:3 petroleum ether-ethyl acetate), to provide an amber colored solid (26.9 g, 93%). 1H NMR (CDCl3) 1.07 (t, 3H), 1.85 (m, 2H), 3.89 (s, 3H), 4.06 (t, 3H), 7.39 (s, 1 H), 7.84 (s, 1 H), 9.81 (s, 1 H).

후처리

  1. temperatureheated for 16 hours
  2. extractionextracted with ether (3×250 mL)
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe organic layer was evaporated by distillation under diminished pressure to an oil
  6. custompurified by column chromatography (silica, 7:3 petroleum ether-ethyl acetate)

출처 및 근거

ORD 기록
ord-de010eadbc7c41288d97e06938c6e170
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05358938

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