4-Coumaric acid → Methyl p-coumarate

HRID 5054

反応式

HRID 5054 の反応式
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[CH3:13]O.S(=O)(=O)(O)O>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([O:10][CH3:13])=[O:9])=[CH:11][CH:12]=1

参加物

4

反応物 3

HCID 3224-Coumaric acidHCID 887MethanolHCID 1118Sulfuric Acid

生成物 1

HCID 92203Methyl p-coumarate収率 77.4%

実験手順

To a 250 mL round bottom flask fitted with a reflux condenser and a nitrogen inlet tube was added 20.0 g (121.8 mmol) 4-hydroxycinnamic acid, 100 mL (246.9 mmol) methanol, and 5.0 g (50.0 mmol) concentrated sulfuric acid. The reaction vessel was heated at 75°-80° C. overnight. After cooling to room temperature, the resulting solution was diluted with 150 mL distilled water, and cooled to 0° C. The resulting precipitate was filtered, washed with sat. NaHCO3 solution, and recrystallized from EtOH/water to afford 16.8 g (77%) methyl 4-hydroxycinnamate which was used without further purification: mp.=139°-140° C.; 1H NMR (CD3SOCD3, 300 MHz) δ 3.42 (broad s, 1H), 3.70 (s, 3H), 6.40 (d, J=16.0 Hz, 1H), 6.81 (d, J=8.4 Hz, 2H), 7.55 (d, J=8.4 Hz, 2H), 7.58 (d, J=16.0 Hz, 1H).

後処理

  1. customTo a 250 mL round bottom flask fitted with a reflux condenser and a nitrogen inlet tube
  2. temperatureThe reaction vessel was heated at 75°-80° C. overnight
  3. additionthe resulting solution was diluted with 150 mL
  4. distillationdistilled water
  5. temperaturecooled to 0° C
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with sat. NaHCO3 solution
  8. customrecrystallized from EtOH/water

出典と根拠

ORDレコード
ord-18f6ecb57450401ca2ce0553ff54682c
出典データセット
uspto-grants-1993_09
特許番号
US05243021

関連ノート

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