Sodium Chloride → 4-Hydroxy-4-methyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

온도

100 °C

In a reaction vessel, water (750 ml) was charged, and the temperature was elevated up to 100° C. to reflux. Then, 5-methyl-2-furylallylcarbinol (24 g) and a solution of MgCl2.6H2O (31.5 g) in water (160 ml) were dropwise added thereto in 2.5 hours and 3.5 hours, respectively. During the addition, the pH value of the reaction mixture was maintained at 5.7 to 5.3 by the addition of an aqueous 10% potassium primary phosphate solution and an aqueous 1 N NaOH solution. After about 1.5 hours from the start of the reaction, the pH value stabilized and remained within said range. After completion of the addition of the aqueous MgCl2 solution, the reaction mixture was stirred at pH 5.5 under reflux at 100° C. for an additional 4.5 hours. Then, the reaction mixture was cooled to 40° C. and neutralized with an aqueous 1 N NaOH solution. After addition of sodium chloride (320 g), the mixture was extracted with toluene (250 ml) four times. The extract was dried over anhydrous magnesium sulfate, and toluene was removed therefrom by distillation at 60° C. under reduced pressure to give an oily substance (21.6 g), which was subjected to distillation under reduced pressure to obtain 2-allyl-3-hydroxy-3-methyl-4-cyclopentenone (20.4 g). Yield, 85%. B.P., 88°-90° C./0.5 mmHg.

1. customwas elevated up to 100° C.
2. temperatureto reflux
3. custom3.5 hours
4. additionDuring the addition
5. customAfter about 1.5 hours from the start of the reaction
6. temperatureThen, the reaction mixture was cooled to 40° C.
7. extractionthe mixture was extracted with toluene (250 ml) four times
8. dry with materialThe extract was dried over anhydrous magnesium sulfate, and toluene
9. customwas removed
10. distillationby distillation at 60° C. under reduced pressure
11. customto give an oily substance (21.6 g), which
12. distillationwas subjected to distillation under reduced pressure

ORD 기록

ord-228a38bc6eaf450d8a335c22cc7b24f6

출처 데이터셋

uspto-grants-1982_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US04356326