反应 #67775

反应方程式

para-Toluene sulfonic acid

2-chloro-3-hydroxypropionic acid

dodecanol

2-chloro-3-hydroxypropionic acid

benzene

→

dodecyl 2-chloro-3-hydroxypropionate

溶剂

CH2Cl2

反应条件

后处理

1. 1
   温度heated at 75° C.-80° C. for 20 h
2. 2
   温度After cooling it down
3. 3
   洗涤Organic phase was washed twice with 50 mL of dil. NaHCO3 aq. sol. and once with 50 mL of sat. NaCl aq. sol.
4. 4
   其他dried over anhy
5. 5
   过滤After filtration
6. 6
   其他removing the solvent
7. 7
   其他by rotary evaporation, yield=7.76 g (78%)
8. 8
   其他It was used for the next reaction without further purification

实验过程

2-chloro-3-hydroxypropionic acid (4.80 g, 0.03 mol), dodecanol (6.00 g, 0.03 mol) were taken with 5 mL dry benzene in a (50 mL) RB, with a dean-stark apparatus and condenser; 25 mg (0.26 mmol) para-Toluene sulfonic acid (pTSA) was added to it and the mixture was stirred at 75° C.-80° C. for 40 h. 1H-NMR showed 85% conversion. More 2-chloro-3-hydroxypropionic acid (1.00 g, 8.00 mmol) was added to it and heated at 75° C.-80° C. for 20 h. 1H-NMR showed almost complete conversion. After cooling it down, the product was added with 100 mL of CH2Cl2. Organic phase was washed twice with 50 mL of dil. NaHCO3 aq. sol. and once with 50 mL of sat. NaCl aq. sol. and then dried over anhy. Na2SO4. After filtration and removing the solvent by rotary evaporation, yield=7.76 g (78%). It was used for the next reaction without further purification. 1H-NMR (CDCl3, 7.27 ppm): 2.18-2.40 (broad, —OH), 3.97 (m, —CH2OH), 4.21 (m, —CO2CH2), 4.39 (m, —CHCl).

来源