Water → 2-Propargyl-3-hydroxy-3-methyl-4-cyclopentenone

HRID 223784

반응식

HRID 223784 반응식
[OH2:1].[CH3:2][C:3]1[O:7][C:6]([CH:8]([CH2:10][C:11]#[CH:12])O)=[CH:5][CH:4]=1.[OH-].[Na+].[Cl-].[Na+]>C([O-])(=O)C.[Na+].C(O)(=O)C>[CH2:10]([CH:8]1[C:3]([OH:7])([CH3:2])[CH:4]=[CH:5][C:6]1=[O:1])[C:11]#[CH:12]

참가 물질

7

반응물 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 14798Sodium Hydroxide2회HCID 98774181-(5-Methylfuran-2-yl)but-3-yn-1-ol

생성물 1

HCID 130367862-Propargyl-3-hydroxy-3-methyl-4-cyclopentenone

시약·촉매·용매 2

HCID 517045Sodium Acetate촉매HCID 176Acetic Acid용매

반응 조건

온도
40 °C

실험 절차

In a reaction vessel, water (1600 ml), anhydrous sodium acetate (0.4 g) and 5-methyl-2-furylpropargylcarbinol (20 g) were charged, and the temperature was elevated to reflux. The pH value was adjusted to 4.5 with an aqueous 0.5 N acetic acid solution, and the mixture was stirred under reflux for 13 hours while maintaining a pH value of 4.0 to 5.0 by the addition of an aqueous 1/3 N NaOH solution. Then, the reaction mixture was cooled to 40° C., neutralized with an aqueous 1/3 N NaOH solution and, after addition of sodium chloride (300 g), extracted with methyl isobutyl ketone (400 ml) five times. From the extract, methyl isobutyl ketone was removed by distillation at 60° c. under reduced pressure to give an oily substance (16 g), which was subjected to distillation under reduced pressure to obtain 2-propargyl-3-hydroxy-3-methyl-4-cyclopentenone (14.8 g). Yield, 74%. B.P., 115°-132° C./0.1 mmHg. nD25 1.5124. C13NMR spectrum (CDCl3, internal standard TMS, δ ppm, 22.6 MHz): 206.2 (1-C); 167.8 (5-C); 130.7 (4-C); 82.0 (--CH2 -C≡CH); 78.5 (3-C); 70.6 (--CH2 --C≡CH); 57.0 (2-C); 23.4 (--CH3); 14.7 (--CH2 --C≡CH).

후처리

  1. temperatureto reflux
  2. temperatureunder reflux for 13 hours
  3. temperaturewhile maintaining a pH value of 4.0 to 5.0
  4. extractionextracted with methyl isobutyl ketone (400 ml) five times
  5. customFrom the extract, methyl isobutyl ketone was removed by distillation at 60° c
  6. customunder reduced pressure to give an oily substance (16 g), which
  7. distillationwas subjected to distillation under reduced pressure

출처 및 근거

ORD 기록
ord-e6226aaea418417284b4319816bfead6
출처 데이터셋
uspto-grants-1982_10
특허 번호
US04356326

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