Hydrochloric Acid → 4-Allyloxy-3-nitrocinnamic acid

HRID 260307

반응식

HRID 260307 반응식
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14])[CH:2]=[CH2:3].C(O)(=O)[CH2:17][C:18]([OH:20])=[O:19].N1CCCCC1.Cl>N1C=CC=CC=1>[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:17][C:18]([OH:20])=[O:19])=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14])[CH:2]=[CH2:3]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 224011524-Allyloxy-3-nitrobenzaldehyde

생성물 1

HCID 543811174-Allyloxy-3-nitrocinnamic acid수율 70.3%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

4-Allyloxy-3-nitrobenzaldehyde (5 g, 24.1 mM) was dissolved in pyridine (100 ml) and malonic acid (5.02 g, 48.3 mM) and piperidine (0.48 ml, 4.8 mM) added. The mixture was heated to reflux with stirring for 2 hours, cooled, and poured onto a mixture of concentrated hydrochloric acid and ice. Organics were extracted into ethyl acetate, the organic layer washed with 2M hydrochloric acid, and product back-extracted into aqueous NaHCO3. The aqueous solution was then re-acidified (concentrated hydrochloric acid), and organics extracted into ethyl acetate, washed with brine, and dried (MgSO4), to give title compound (4.23 g).

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturecooled
  4. extractionOrganics were extracted into ethyl acetate
  5. washthe organic layer washed with 2M hydrochloric acid, and product
  6. extractionback-extracted into aqueous NaHCO3
  7. extractionre-acidified (concentrated hydrochloric acid), and organics extracted into ethyl acetate
  8. washwashed with brine
  9. dry with materialdried (MgSO4)

출처 및 근거

ORD 기록
ord-2d00ecb238134095b6b0426401ec41a6
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05527791

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