反応 #67775

反応方程式

para-Toluene sulfonic acid

2-chloro-3-hydroxypropionic acid

dodecanol

2-chloro-3-hydroxypropionic acid

benzene

→

dodecyl 2-chloro-3-hydroxypropionate

溶媒

CH2Cl2

反応条件

後処理

1. 1
   温度heated at 75° C.-80° C. for 20 h
2. 2
   温度After cooling it down
3. 3
   洗浄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
   その他dried over anhy
5. 5
   ろ過After filtration
6. 6
   その他removing the solvent
7. 7
   その他by rotary evaporation, yield=7.76 g (78%)
8. 8
   その他It was used for the next reaction without further purification

実験手順

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).

出典