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

HRID 77663

反応式

HRID 77663 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:10][C:11]([CH3:13])=[O:12].[OH-].[Na+].O>C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:10][C:11](=[O:12])[CH:13]=[CH:1][C:2]2[CH:9]=[CH:8][CH:7]=[C:4]([CH3:5])[CH:3]=2)[CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 180AcetoneHCID 962WaterHCID 121053-MethylbenzaldehydeHCID 14798Sodium Hydroxide

生成物 1

HCID 34562181,5-Bis(3-methylphenyl)-1,4-pentadien-3-one収率 72%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

3-Methylbenzaldehyde (1ab, 3.00 ml, 25.4 mmol) and acetone (19, 0.94 ml, 12.7 mmol) were combined in ethanol (20 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (1.50 g, 37.5 mmol) and water (20 ml) was added and the mixture stirred for 18 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 2.39 g (72%) of a yellow solid: mp 68-72° C. [expected mp 68-72° C.]; 1H NMR: δ 2.38 (s, 6H), 7.06 (d, 2H, J=15.9 Hz), 7.26 (m, 4H), 7.40 (m, 4H), 7.70 (d, 2H, J=15.9 Hz); 13C NMR: δ 21.3, 125.1, 125.4, 128.6, 128.8, 131.1, 134.6, 138.4, 143.1, 188.6.

後処理

  1. stirringthe mixture stirred for 18 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-5092852dab894a7c83a10adce66f037a
出典データセット
uspto-grants-2014_09
特許番号
US08841326B2

関連ノート

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