4'-Hydroxyacetophenone → 4-Hydroxy-3-Nitroacetophenone

HRID 964617

반응식

HRID 964617 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[N+:11]([O-])([O-:13])=[O:12].[K+]>[N+]([O-])([O-])=O.[K+].OS(O)(=O)=O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

참가 물질

5

반응물 2

HCID 74694'-HydroxyacetophenoneHCID 24434Potassium Nitrate

생성물 1

HCID 1387234-Hydroxy-3-Nitroacetophenone수율 94.7%

시약·촉매·용매 2

HCID 24434Potassium Nitrate촉매HCID 1118Sulfuric Acid용매

실험 절차

To mechanically stirred conc. H2SO4 (700 mL) at 3° C. was added p-hydroxyacetophenone (66.0 g, 480 mmol) followed by KNO3 (48.3 g, 477 mmol) in two approximately equal portions about four minutes apart. An additional 3.76 g of KNO3 was added after 1.67 hours to insure reaction completion. The reaction was slowly poured into 8 L crushed ice/water and extracted with 4 L ethyl acetate (EtOAc). The extract was concentrated in vacuo to a volume of ~1.25 L, 500 mL heptane were added and concentration was continued. Once a thick yellow suspension formed at 50° C., it was cooled to ~10° C. and filtered. The collected solids were washed with ~150 mL heptane and dried in vacuo at ~40° C. to give 81.8 g of the title compound.

후처리

  1. customreaction completion
  2. additionThe reaction was slowly poured into 8 L
  3. extractionextracted with 4 L ethyl acetate (EtOAc)
  4. concentrationThe extract was concentrated in vacuo to a volume of ~1.25 L, 500 mL heptane
  5. additionwere added
  6. concentrationconcentration
  7. customOnce a thick yellow suspension formed at 50° C.
  8. temperatureit was cooled to ~10° C.
  9. filtrationfiltered
  10. washThe collected solids were washed with ~150 mL heptane
  11. customdried in vacuo at ~40° C.

출처 및 근거

ORD 기록
ord-1b9405fe1d3b454593f3511a1cfa4c43
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05770615

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