3-Hydroxybenzaldehyde → 3-Isopropoxybenzaldehyde

HRID 48070

반응식

HRID 48070 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].I[CH:11]([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].O>C(O)(C)C>[CH:11]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])([CH3:13])[CH3:12]

참가 물질

6

반응물 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium Carbonate

생성물 1

HCID 7129143-Isopropoxybenzaldehyde수율 67%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

Ex-645A) 3-Hydroxybenzaldehyde (5.60 g, 45.9 mmol) and 2-iodopropane (7.86 g, 46.2 mmol) were dissolved in 50 mL of isopropanol. Potassium carbonate (20 g, 145 mmol) was added, and the mixture was heated to reflux for 8 h, at which time TLC analysis indicated that the reaction had gone to completion. Water was added to dissolve all solids, and the mixture was extracted with ether (3×). The combined ether layer was washed with water, 2 M NaOH, again with water until clear (4×), and finally with brine. The solution was dried over MgSO4, filtered, and evaporated to give 5.03 g (67%) of the desired 3-isopropoxybenzaldehyde product as a pale oil. 1H NMR (C6D6) δ9.62 (s, 1H), 7.29 (s, 1H), 7.03 (m, 1H), 6.91 (t, 1H), 6.84 (m, 1H), 4.03 (septet, 1H), 0.96 (d, 6H).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 8 h, at which time TLC analysis
  3. dissolutionto dissolve all solids
  4. extractionthe mixture was extracted with ether (3×)
  5. washThe combined ether layer was washed with water, 2 M NaOH, again with water until clear (4×)
  6. dry with materialThe solution was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-9875bb0e6b004f91984fa7af87dd41f1
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699898B2

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