Hydrochloric Acid → HCID 97793, 화합물

HRID 707737노트

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HRID 707737 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

HCID 97793HCID 97793, 화합물

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-954c53397e1f40aab6bcef0514626857
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09175123B2

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