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

HRID 1980617노트

반응식

HRID 1980617 반응식
C([O-])(=[O:3])C.[Na+].C(O)(=O)C.[CH3:10][C:11]1[O:15][C:14]([CH:16]=[CH:17][CH2:18][CH2:19]O)=[CH:13][CH:12]=1.[Cl-].[Na+]>O>[CH2:17]([C:16]1[C:14](=[O:15])[CH2:13][CH:12]([OH:3])[C:11]=1[CH3:10])[CH:18]=[CH2:19]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 517045Sodium AcetateHCID 704783345-Methyl-2-furylallylcarbinol

생성물 1

HCID 110832-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-수율 209.3%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A buffer solution was prepared by dissolving sodium acetate (1.03 g) and MgCl2.6H2O (0.27 g) in water (200 ml) and adjusting the pH value to 6.0 (20° C.) with acetic acid. In a reaction vessel, 5-methyl-2-furylallylcarbinol (5 g) and the entire amount of the buffer solution as prepared above were charged, and the temperature was elevated up to 150° C. in 35 minutes while stirring. The mixture was stirred at the same temperature for 3 hours. After ice-cooling, sodium chloride (50 g) was added, and the mixture was extracted with methyl isobutyl ketone (100 ml) four times. The extract was concentrated at 60° C. under reduced pressure to remove methyl isobutyl ketone, whereby an oily substance (4.6 g) was obtained. The crude product was purified by column chromatography with silica gel (60 g) (developing solvent, ethyl acetate-n-hexane (1:2 by volume)) to obtain 2-allyl-3-methyl-4-hydroxy-2-cyclopentenone (4.0 g). Yield, 80%.

후처리

  1. customA buffer solution was prepared
  2. customto 6.0 (20° C.)
  3. additionabove were charged
  4. stirringThe mixture was stirred at the same temperature for 3 hours
  5. temperatureAfter ice-cooling
  6. extractionthe mixture was extracted with methyl isobutyl ketone (100 ml) four times
  7. concentrationThe extract was concentrated at 60° C. under reduced pressure
  8. customto remove methyl isobutyl ketone, whereby an oily substance (4.6 g)
  9. customwas obtained
  10. customThe crude product was purified by column chromatography with silica gel (60 g) (developing solvent, ethyl acetate-n-hexane (1:2 by volume))

출처 및 근거

ORD 기록
ord-6a1be963fad348f8b53d43fee6b90076
출처 데이터셋
uspto-grants-1985_04
특허 번호
US04510329

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