Acetone → 4-(4-Methoxyphenyl)but-3-en-2-one

HRID 714188

反応式

HRID 714188 の反応式
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH3:11][C:12]([CH3:14])=[O:13].[OH-].[Na+].O>C(O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH:11][C:12](=[O:13])[CH3:14])=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 312444-Methoxybenzaldehyde

生成物 1

HCID 954144-(4-Methoxyphenyl)but-3-en-2-one収率 62.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

4-Methoxybenzaldehyde (1e, 0.63 ml, 5.2 mmol) and acetone (19, 4.00 ml, 54.0 mmol) were combined in ethanol (4 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (0.40 g, 10.0 mmol) and water (4 ml) was added dropwise and the mixture stirred for 1 hr at room temperature. The resulting mixture was extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from ether/hexane to give 0.57 g (62%) of a yellow solid: mp 71-73° C. [expected mp 68° C.]; 1H NMR: δ 2.34 (s, 3H), 3.83 (s, 3H), 6.59 (d, 1H, 0.1=16.3 Hz), 6.90 (d, 2H, J=8.7 Hz), 7.46 (d, 1H, J=16.3 Hz), 7.48 (d, 2H, J=8.7 Hz); 13C NMR: δ 27.5, 55.4, 114.4, 125.0, 127.1, 129.9, 143.1, 161.5, 198.1.

後処理

  1. stirringthe mixture stirred for 1 hr at room temperature
  2. extractionThe resulting mixture was extracted into ethyl acetate
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a solid
  8. customThe crude solid was recrystallized from ether/hexane

出典と根拠

ORDレコード
ord-e6478123efe24862922cb7c8b01d81d6
出典データセット
uspto-grants-2015_11
特許番号
US09187397B2

関連ノート

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