Sulfuric Acid → 6-nitro-3,4-dihydro-2H-1-benzopyran-4-one

HRID 2200198노트

반응식

HRID 2200198 반응식
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].OS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[N+:1]([C:4]1[CH:5]=[C:6]2[C:7](=[CH:14][CH:15]=1)[O:8][CH2:9][CH2:10][C:11]2=[O:13])([O-:3])=[O:2]

참가 물질

4

반응물 3

HCID 1118Sulfuric AcidHCID 14812Phosphorus oxide (P4O10)HCID 3515353-(4-Nitrophenoxy)propionic acid

생성물 1

HCID 52288316-nitro-3,4-dihydro-2H-1-benzopyran-4-one수율 79.4%

반응 조건

온도
65 °C

실험 절차

Mix 3-(4-nitrophenoxy)propanoic acid (6.5 g, 30 mmol) and concentrated H2SO4 (30 mL). Once dissolved, add P2O5, stir at 65° C. for 3 hrs. Cool to room temperature, pour slowly the reaction mixture to ice water (50 mL), stir for 15 min, and extract with EtOAc (100 mL×3). Combine the organic layers, wash with brine (100 mL×2), dry over anhydrous Na2SO4, concentrate to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=1:1) affords the title compound (4.6 g, 77.8%). MS: (M−1): 192.2.

후처리

  1. dissolutionOnce dissolved
  2. temperatureCool to room temperature
  3. stirringstir for 15 min
  4. extractionextract with EtOAc (100 mL×3)
  5. washCombine the organic layers, wash with brine (100 mL×2)
  6. dry with materialdry over anhydrous Na2SO4
  7. concentrationconcentrate
  8. customto give the crude product
  9. customPurification by chromatography (silica gel, EtOAc:PE=1:1)

출처 및 근거

ORD 기록
ord-6bee8db22a9440a88af444146e61f857
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359338B2

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