반응 #67775

반응 방정식

para-Toluene sulfonic acid

2-chloro-3-hydroxypropionic acid

dodecanol

2-chloro-3-hydroxypropionic acid

benzene

→

dodecyl 2-chloro-3-hydroxypropionate

용매

CH2Cl2

반응 조건

후처리

1. 1
   온도heated at 75° C.-80° C. for 20 h
2. 2
   온도After cooling it down
3. 3
   세척Organic phase was washed twice with 50 mL of dil. NaHCO3 aq. sol. and once with 50 mL of sat. NaCl aq. sol.
4. 4
   기타dried over anhy
5. 5
   여과After filtration
6. 6
   기타removing the solvent
7. 7
   기타by rotary evaporation, yield=7.76 g (78%)
8. 8
   기타It was used for the next reaction without further purification

실험 절차

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).

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