Reaction #65577

Reaction equation

hexane ethyl ether

methyl 3-cyclododecylprop-2-enoate

magnesium

→

title compound

Yield 61.3%

3-Cyclododecylpropanoic acid, methyl ester

Yield 61.3%

Solvents

methanol

Conditions

Workup

1. 1
   Temperature(ice bath cooling is applied when necessary to control exothermic excursions)
2. 2
   Extractionis extracted with ethyl ether (3 times)
3. 3
   WashThe combined ethereal extracts are washed with 2N hydrochloric acid
4. 4
   Dryingare dried over magnesium sulfate
5. 5
   FiltrationFiltration and evaporation
6. 6
   Othergives an oily solid
7. 7
   Washas eluting solvent

Procedure

To a solution of 12.6 g (50 mmol) of methyl 3-cyclododecylprop-2-enoate in 100 ml of methanol is added 3.6 g (150 mmol), 3 equiv) of magnesium metal (activated by prior heating to 160° C.) and the mixture is stirred at room temperature for 2 hours (ice bath cooling is applied when necessary to control exothermic excursions). The reaction mixture is digested with ice cold 2N hydrochloric acid and is extracted with ethyl ether (3 times). The combined ethereal extracts are washed with 2N hydrochloric acid and are dried over magnesium sulfate. Filtration and evaporation gives an oily solid. Flash chromatography on silica gel using hexane/ethyl ether (10:1) as eluting solvent affords 7.80 g of the title compound: IR 1748cm-1 ; NMR (CDCl3) δ 1.33 (m, 23H), 1.54 (t, 2H, J=8 Hz), 2.31 (t, 2H, J=8 Hz), 3.66(s, 3H).

Source