Hydrochloric Acid → HCID 97793、化合物

HRID 707737ノート

反応式

HRID 707737 の反応式
[OH-].[Na+].[CH3:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[CH:10][CH:11]=1)=[O:5].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.Cl>C1COCC1.ClCCl.CO.O>[OH:12][C:9]1[CH:10]=[CH:11][C:6]([C:4](=[O:5])[CH:3]=[CH:19][C:18]2[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)=[CH:7][CH:8]=1

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 74694'-HydroxyacetophenoneHCID 14798Sodium HydroxideHCID 312444-Methoxybenzaldehyde

生成物 1

HCID 97793HCID 97793、化合物

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of sodium hydroxide (100 g, 2.50 mol) in 1.8 L of a 10:8 mixture of water and methanol was added 4-hydroxyacetophenone (136 g, 1.00 mol). After stirring at room temperature for 30 minutes, 4-Methoxybenzaldehyde (136 g, 1.00 mol) was added to this mixture. The reaction mixture was stirred at 50° C. oil bath for 16 hours. A clear yellow solution resulted which was allowed to stir at room temperature for 30 minutes. 1N HCl aq (500 mL) and 600 mL of a 1:1 mixture of dichloromethane and THF were added to result two layers. The organic layer was washed by saturated NaHCO3 aq. (300 mL×2) and water (300 mL×3) and evaporated to yield orange solid. This solid was washed by 300 mL of EtOAc two times. The resulted yellow solid was dried in vacuo. Yield 133 g (52%). 1H NMR (CDCl3): δ3.85 (s, 3H), 6.93 (m, 4H), 7.47 (d, 1H), 7.50 (d, 2H), 7.75 (d, 1H), 7.96 (d, 2H).

後処理

  1. stirringThe reaction mixture was stirred at 50° C. oil bath for 16 hours
  2. customA clear yellow solution resulted which
  3. stirringto stir at room temperature for 30 minutes
  4. additionwere added
  5. customto result two layers
  6. washThe organic layer was washed by saturated NaHCO3 aq. (300 mL×2) and water (300 mL×3)
  7. customevaporated
  8. customto yield orange solid
  9. washThis solid was washed by 300 mL of EtOAc two times
  10. customThe resulted yellow solid was dried in vacuo

出典と根拠

ORDレコード
ord-954c53397e1f40aab6bcef0514626857
出典データセット
uspto-grants-2015_11
特許番号
US09175123B2

反応ノート

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