Acetone → 1,5-Bis(2-methylphenyl)-1,4-pentadien-3-one

HRID 77664ノート

反応式

HRID 77664 の反応式
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][C:11]([CH3:13])=[O:12].[OH-].[Na+].O>C(O)C>[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH:10][C:11](=[O:12])[CH:13]=[CH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH3:4]

参加物

6

反応物 4

HCID 180AcetoneHCID 962WaterHCID 107222-MethylbenzaldehydeHCID 14798Sodium Hydroxide

生成物 1

HCID 45639421,5-Bis(2-methylphenyl)-1,4-pentadien-3-one収率 43.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

2-Methylbenzaldehyde (1ac, 1.45 ml, 12.5 mmol) and acetone (19, 0.46 ml, 6.3 mmol) were combined in ethanol (20 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (2.61 g, 65.3 mmol) and water (25 ml) was added and the mixture stirred for 3 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 ethanol to give 0.71 g (43%) of a yellow solid: mp 98-100° C. [expected mp 94-96° C.]; 1H NMR: δ 2.47 (s, 6H), 6.98 (d, 2H, J=15.9 Hz), 7.24 (m, 6H), 7.64 (d, 2H, J=7.2 Hz), 8.03 (d, 2H, J=15.9 Hz); 13C NMR: δ 19.7, 126.1, 126.2, 126.5, 129.9, 130.7, 133.6, 137.9, 140.5, 188.5.

後処理

  1. stirringthe mixture stirred for 3 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 ethanol

出典と根拠

ORDレコード
ord-fc1f282e551a4b55939d9e559b61ed9f
出典データセット
uspto-grants-2014_09
特許番号
US08841326B2

反応ノート

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