Water → 2-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-

HRID 68018

反応式

HRID 68018 の反応式
O[C:2]1([CH3:11])[CH:6]([CH2:7][CH:8]=[CH2:9])[C:5](=[O:10])[CH:4]=[CH:3]1.[Na+].[Cl-].[OH2:14]>[Cl-].[Cl-].[Zn+2]>[CH2:7]([C:6]1[C:5](=[O:10])[CH2:4][CH:3]([OH:14])[C:2]=1[CH3:11])[CH:8]=[CH2:9]

参加物

5

反応物 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 128798724-Hydroxy-4-methyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

生成物 1

HCID 110832-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-

試薬・触媒・溶媒 1

HCID 3007855Zincchloride触媒

実験手順

Into a reaction vessel, a solution of 4-hydroxy-4-methyl-5-allyl-2-cyclopentenone (3 g) and ZnCl2 (5 g) in water (120 ml) was charged, and the temperature was elevated up to 100° C. The contents were refluxed for 15 hours while stirring. After cooling, NaCl (40 g) was added to the reaction mixture, and the resulting mixture was extracted with toluene (120 ml) 4 times. The extracts were combined together and concentrated at 50° C. under reduced pressure to give an oily substance (2.5 g). The oily substance was chromatographed on silica gel (30 g), followed by development with a solvent mixture of ethyl acetate and hexane (1:2 by volume) to give 2-allyl-3-methyl-4-hydroxy-2cyclopentenone (2.4 g). Yield, 80%.

後処理

  1. customwas elevated up to 100° C
  2. temperatureThe contents were refluxed for 15 hours
  3. temperatureAfter cooling
  4. extractionthe resulting mixture was extracted with toluene (120 ml) 4 times
  5. concentrationconcentrated at 50° C. under reduced pressure
  6. customto give an oily substance (2.5 g)
  7. customThe oily substance was chromatographed on silica gel (30 g)
  8. additionfollowed by development with a solvent mixture of ethyl acetate and hexane (1:2 by volume)

出典と根拠

ORDレコード
ord-7436dd597eeb4c6c8844966dbf67a313
出典データセット
uspto-grants-1982_08
特許番号
US04347386

関連ノート

読み込み中…