Acetone → 4-[3-Methoxy-4-(methoxymethoxy)phenyl]but-3-en-2-one

HRID 714189ノート

反応式

HRID 714189 の反応式
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][C:6]=1[O:13][CH3:14].[CH3:15][C:16]([CH3:18])=[O:17].[OH-].[Na+].O>C(O)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:15][C:16](=[O:17])[CH3:18])=[CH:7][C:6]=1[O:13][CH3:14]

参加物

6

反応物 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 796613-Methoxy-4-(methoxymethoxy)benzaldehyde

生成物 1

HCID 695016824-[3-Methoxy-4-(methoxymethoxy)phenyl]but-3-en-2-one収率 97.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

4-Methoxymethyloxy-3-methoxybenzaldehyde (1j, 2.30 g, 11.7 mmol) and acetone (19, 8.75 ml, 118.4 mmol) were combined in ethanol (20 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (0.80 g, 20.0 mmol) and water (20 ml) was added 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 hexane to give 2.70 g (97%) of a white solid: mp 73-75° C.; 1H NMR: δ 2.34 (s, 3H), 3.48 (s, 3H), 3.89 (s, 3H), 5.24 (s, 2H), 6.58 (d, 1H, J=16.1 Hz), 7.07 (m, 2H), 7.13 (d, 1H, J=8.7 Hz), 7.43 (d, 1H, J=16.1 Hz); 13C NMR: δ 27.4, 55.9, 56.3, 95.2, 110.4, 115.9, 122.5, 125.7, 128.7, 143.1, 148.7, 149.8, 198.0.

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 hexane

出典と根拠

ORDレコード
ord-738f3df2774248cd809c7e3afb861164
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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