反应 #543566

反应方程式

potassium hydroxide

hexadecyl bromide

D-Acetone glycerol

→

1-hexadecyl-glyceryl ether

收率 77.2%

溶剂

ether

benzene

反应条件

后处理

1. 1
   温度refluxed for 5 hours
2. 2
   其他while removing the water
3. 3
   其他formed by azeotropic distillation (compare W. J. Baumann and H. K. Mangold, J. Org. Chem. 29: 3055, 1964 and F. Paltauf, Monatsh. 99:1277, 1968)
4. 4
   洗涤The resulting solution was washed with water (2×50 ml)
5. 5
   其他the solvent was removed under reduced pressure
6. 6
   workup.ADDITIONA 100 ml mixture of 90:10:5 methanol:water:concentrated hydrochloric acid was added to the residue
7. 7
   温度the mixture was refluxed for 10 minutes
8. 8
   萃取The product was extracted with ether (200 ml)
9. 9
   洗涤was washed consecutively with water (50 ml), 10% sodium hydroxide (20 ml) and again with water (volumes of 20 ml) until neutral
10. 10
    其他The solvent was removed under reduced pressure
11. 11
    其他the product (8.8 grams) was crystallized from hexane

实验过程

D-Acetone glycerol (4 grams) for synthesis of L-ALLE or L-Acetone glycerol for synthesis of D-ALLE, powdered potassium hydroxide (approximately 10 grams) and hexadecyl bromide (9.3 grams) in benzene (100 ml) were stirred and refluxed for 5 hours, while removing the water formed by azeotropic distillation (compare W. J. Baumann and H. K. Mangold, J. Org. Chem. 29: 3055, 1964 and F. Paltauf, Monatsh. 99:1277, 1968). The volume of the solvent was gradually reduced to about 20 ml, and the resulting mixture was cooled to room temperature and dissolved in ether (100 ml). The resulting solution was washed with water (2×50 ml), and the solvent was removed under reduced pressure. A 100 ml mixture of 90:10:5 methanol:water:concentrated hydrochloric acid was added to the residue and the mixture was refluxed for 10 minutes. The product was extracted with ether (200 ml) and was washed consecutively with water (50 ml), 10% sodium hydroxide (20 ml) and again with water (volumes of 20 ml) until neutral. The solvent was removed under reduced pressure and the product (8.8 grams) was crystallized from hexane to give 7.4 grams of pure 1-hexadecyl-glyceryl ether (compound I, FIG. 1) for synthesis of D-ALLE or 3-hexadecyl-glyceryl ether for synthesis of L-ALLE.

来源