Acrolein → 6-Hydroxychromene-3-carboxaldehyde

HRID 466174

반응식

HRID 466174 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=O.C(=O)([O-])[O-].[K+].[K+].[CH:17]([CH:19]=[CH2:20])=[O:18]>O1CCOCC1>[OH:10][C:7]1[CH:8]=[CH:9][C:2]2[O:1][CH2:20][C:19]([CH:17]=[O:18])=[CH:4][C:3]=2[CH:6]=1

참가 물질

5

반응물 3

HCID 7847AcroleinHCID 11430Potassium CarbonateHCID 709492,5-Dihydroxybenzaldehyde

생성물 1

HCID 47708156-Hydroxychromene-3-carboxaldehyde

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

The starting material is prepared as follows: 2,5-Dihydroxybenzaldehyde (25.0 g, 0.18 mol) is dissolved in 375 ml of 1,4-dioxane. To this is sequentially added potassium carbonate (50.0 g, 0.36 mol) and acrolein (15.22 g, 0.27 mol). The mixture is heated at reflux overnight, cooled, and partitioned between water and ether. The aqueous layer is removed and extracted twice with ether. The combined organic layers are dried (MgSO4) and evaporated. Trituration of the residue with dichloromethane, followed by filtration and drying, yields 6-hydroxy-2H-1-benzopyran-3-carboxaldehyde, m.p. 163°-165° C., as a yellow crystalline solid.

후처리

  1. customThe starting material is prepared
  2. temperatureThe mixture is heated
  3. temperatureat reflux overnight
  4. temperaturecooled
  5. custompartitioned between water and ether
  6. customThe aqueous layer is removed
  7. extractionextracted twice with ether
  8. dry with materialThe combined organic layers are dried (MgSO4)
  9. customevaporated
  10. filtrationTrituration of the residue with dichloromethane, followed by filtration
  11. customdrying

출처 및 근거

ORD 기록
ord-763ad5d4fe4f4ca6b62819782459a78d
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155130

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