Ethoxyacetic acid synthesis
- Product Name:Ethoxyacetic acid
- CAS Number:627-03-2
- Molecular formula:C4H8O3
- Molecular Weight:104.1
64-17-5
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$10.00/50g
3926-62-3
258 suppliers
$16.69/250g
627-03-2
174 suppliers
$21.21/5gm:
Yield:627-03-2 76%
Reaction Conditions:
Stage #1:ethanol with sodium at 60;
Stage #2:sodium monochloroacetic acid with N-benzyl-N,N,N-triethylammonium chloride for 8 h;Reflux;
Steps:
4 Synthesis of 2-ethoxyacetic acid
Sodium (5.00 g, 0.217 mol) was dissolved in abs ethanol (250 mL) at 60 °C, then triethylbenzylammonium chloride (TEBA-Cl, 0.50 g, 0.018 mol) and sodium chloroacetate (20.00 g, 0.172 mol) were added to the solution.
The mixture was refluxed for 8 h then ethanol was removed under vacuum.
The residue was dissolved in water (200 mL) and 5N HCl was added (to pH=2).
The solution was extracted with ethyl acetate (3*100 mL).
The organic phases were unified and washed with brine (50 mL), dried over MgSO4.
After removal of the solvent by vacuum rotary evaporation, the residue was purified with vacuum distillation to yield 2-ethoxyacetic acid as a colorless oil.
Yield: 13.68 g (76%); bp=105 °C (16 Torr); nD20=1.4190; dH (300 MHz CDCl3) 1.23 (3H, t, J=6.97 Hz, CH3), 3.59 (2H, q, J=6.95 Hz, CH2), 4.09 (2H, s, CH2), 8.27 (1H, s, OH); dC (75 MHz CDCl3): 175.22, 67.60, 67.50, 15.00; nmax (liquid film): 2979, 2898, 1725, 1430, 1350, 1205, 1113, 1031, 1008, 877, 848, and 669 cm-1.
References:
Oláh, Márk;Boros, Zoltán;Hornyánszky, Gábor;Poppe, László [Tetrahedron,2016,vol. 72,# 46,p. 7249 - 7255]
817-95-8
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$49.00/5g
627-03-2
174 suppliers
$21.21/5gm:
110-80-5
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$10.00/25ml
627-03-2
174 suppliers
$21.21/5gm: