Hydrochloric Acid → 4-Hydroxy-4-methyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

HRID 223787

반응식

HRID 223787 반응식
Cl.[OH-:2].[Na+].[CH3:4][C:5]1[O:9][C:8]([CH:10]=[CH:11][CH2:12][CH2:13]O)=[CH:7][CH:6]=1.[Cl-].[Na+]>[Cl-].C([N+](CCCCCCCC)(CCCCCCCC)C)CCCCCCC.C(OCC)(=O)C.CCCCCC.O>[CH2:11]([CH:10]1[C:5]([OH:9])([CH3:4])[CH:6]=[CH:7][C:8]1=[O:2])[CH:12]=[CH2:13]

참가 물질

8

반응물 4

HCID 313Hydrochloric Acid2회HCID 5234Sodium ChlorideHCID 14798Sodium Hydroxide2회HCID 704783345-Methyl-2-furylallylcarbinol

생성물 1

HCID 128798724-Hydroxy-4-methyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

시약·촉매·용매 3

HCID 21218Trioctylmethylammonium chloride촉매HCID 962Water용매HCID 21226206Ethyl acetate hexane용매

반응 조건

온도
40 °C

실험 절차

In a reaction vessel, water (150 ml) and tri-n-octylmethylammonium chloride (450 mg) were charged, and the pH value was adjusted to 5.5 with an aqueous 1/3 N HCl solution and an aqueous 1/3 N NaOH solution. Then, 5-methyl-2-furylallylcarbinol (11.0 g) was added thereto, and the temperature was elevated up to 100° C. to reflux. The mixture was stirred under reflux for 7 hours while maintaining a pH value of 5 to 5.5 by the addition of an aqueous 1/3 N NaOH solution and an aqueous 1/3 N HCl solution. After cooling to 40° C., sodium chloride (30 g) was added, and the mixture was extracted with toluene (70 ml) five times. From the extract, toluene was removed by distillation at 60° C. under reduced pressure to give an oily substance (10.1 g), which was subjected to chromatography on silica gel (100 g) with a mixture of ethyl acetate-n-hexane (1:2 by volume) as the developing solvent to obtain 2-allyl-3-hydroxy-3-methyl-4-cyclopentenone (7.1 g). Yield, 64.5%.

후처리

  1. customwas elevated up to 100° C.
  2. temperatureto reflux
  3. temperatureunder reflux for 7 hours
  4. temperaturewhile maintaining a pH value of 5 to 5.5
  5. extractionthe mixture was extracted with toluene (70 ml) five times
  6. customFrom the extract, toluene was removed by distillation at 60° C. under reduced pressure
  7. customto give an oily substance (10.1 g), which

출처 및 근거

ORD 기록
ord-7a2f7977e2b24c78a063cc12662764ef
출처 데이터셋
uspto-grants-1982_10
특허 번호
US04356326

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