Réaction #67775

Équation de réaction

para-Toluene sulfonic acid

2-chloro-3-hydroxypropionic acid

dodecanol

2-chloro-3-hydroxypropionic acid

benzene

→

dodecyl 2-chloro-3-hydroxypropionate

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Températureheated at 75° C.-80° C. for 20 h
2. 2
   TempératureAfter cooling it down
3. 3
   LavageOrganic phase was washed twice with 50 mL of dil. NaHCO3 aq. sol. and once with 50 mL of sat. NaCl aq. sol.
4. 4
   Autredried over anhy
5. 5
   FiltrationAfter filtration
6. 6
   Autreremoving the solvent
7. 7
   Autreby rotary evaporation, yield=7.76 g (78%)
8. 8
   AutreIt was used for the next reaction without further purification

Mode opératoire

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).

Source