Acrolein → 6-Hydroxychromene-3-carboxaldehyde

HRID 466174

反応式

HRID 466174 の反応式
[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

参加物

5

反応物 3

HCID 7847AcroleinHCID 11430Potassium CarbonateHCID 709492,5-Dihydroxybenzaldehyde

生成物 1

HCID 47708156-Hydroxychromene-3-carboxaldehyde

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-763ad5d4fe4f4ca6b62819782459a78d
出典データセット
uspto-grants-1992_10
特許番号
US05155130

関連ノート

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