Acetone → 1,4-Pentadien-3-one, 1,5-bis(3-chlorophenyl)-

HRID 714175ノート

反応式

HRID 714175 の反応式
[Cl: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>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:10][C:11](=[O:12])[CH:13]=[CH:5][C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[CH:3]=2)[CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 180AcetoneHCID 962WaterHCID 114773-ChlorobenzaldehydeHCID 14798Sodium Hydroxide

生成物 1

HCID 27759911,4-Pentadien-3-one, 1,5-bis(3-chlorophenyl)-収率 90.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

3-Chlorobenzaldehyde (1y, 2.00 ml, 17.7 mmol) and acetone (19, 0.65 ml, 8.8 mmol) were combined in ethanol (20 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (1.00 g, 25.0 mmol) and water (20 ml) was added and the mixture stirred for 2 hr at room temperature. The resulting precipitate was filtered and recrystallized from ethyl acetate to give 2.41 g (90%) of a yellow solid: mp 125-127° C. [expected mp 120-121° C.]; 1H NMR: δ 7.03 (d, 2H, J=15.9 Hz), 7.33 (m, 4H), 7.45 (d, 2H, J=6.6 Hz), 7.58 (m, 2H), 7.64 (d, 2H, J=15.9 Hz); 13C NMR: δ 126.3, 126.6, 127.9, 130.1, 130.3, 134.9, 136.5, 141.8, 188.0.

後処理

  1. stirringthe mixture stirred for 2 hr at room temperature
  2. filtrationThe resulting precipitate was filtered
  3. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-262e2223e9e945098e553d5fcc6d88a9
出典データセット
uspto-grants-2015_11
特許番号
US09187397B2

反応ノート

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