3-Hydroxybenzaldehyde → 3-Isopropoxybenzaldehyde

HRID 48070

反応式

HRID 48070 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 7129143-Isopropoxybenzaldehyde収率 67%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9875bb0e6b004f91984fa7af87dd41f1
出典データセット
uspto-grants-2004_03
特許番号
US06699898B2

関連ノート

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