海萝胶 → 4-Allyloxy-3-nitrocinnamic acid

HRID 260307

反应方程式

HRID 260307 反应方程式
[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]

参与物

6

反应物 4

HCID 313海萝胶HCID 867丙二酸HCID 8082六氢吡啶HCID 224011524-Allyloxy-3-nitrobenzaldehyde

产物 1

HCID 543811174-Allyloxy-3-nitrocinnamic acid收率 70.3%

试剂、催化剂与溶剂 1

HCID 1049吡啶溶剂

实验过程

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).

后处理

  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)

来源与证据

ORD记录
ord-2d00ecb238134095b6b0426401ec41a6
来源数据集
uspto-grants-1996_06
专利号
US05527791

关联笔记

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