Tetradecylthioacetic acid synthesis
- Product Name:Tetradecylthioacetic acid
- CAS Number:2921-20-2
- Molecular formula:C16H32O2S
- Molecular Weight:288.49
Yield:2921-20-2 94%
Reaction Conditions:
Stage #1:1-Bromotetradecane;mercaptoacetic acid with methanol;potassium hydroxide at 20;
Stage #2: with hydrogenchloride in water
Steps:
1 Preparation of tetradecylthioacetic Acid
Potassium hydroxide (34.30 g, 0.611 mol), mercaptoacetic acid (20.9 ml, 0.294 mol) and 1-bromotetradecane (50 ml, 0.184 mol) were added in that order to methanol (400 ml). The mixture was stirred overnight at room temperature. A concentrated hydrochloric acid solution (60 ml) dissolved in water (800 ml) was then added. The tetradecylthioacetic acid precipitated. The mixture was stirred overnight at room temperature. The precipitate was then filtered, washed five times with water and dried in a dessicator. The product was recrystallized in methanol. Yield: 94% Rf (dichloromethane/methanol 9:1): 0.60 MP: 67-68° C. IR: νCO acid 1726 and 1684 cm-1 NMR (1H, CDCl3): 0.84-0.95 (t, 3H, -CH3, J=6.5 Hz); 1.20-1.45 (multiplet, 22H, -CH2-); 1.55-1.69 (quint, 2H, -CH2-CH2-S-, J=7 Hz); 2.63-2.72 (t, 2H, CH2-CH2-S-, J=7 Hz); 3.27 (s, 2H, S-CH2-COOH) MS (ESI-MS): M-1=287.
References:
Darteil, Raphael;Caumont-Bertrand, Karine;Najib, Jamila US2006/69156, 2006, A1 Location in patent:Page/Page column 20
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