Magnesium → 3-Cyclododecylpropanoic acid, methyl ester

HRID 2380358Notes

Reaction equation

[CH:1]1([CH:13]=[CH:14][C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Mg].CCCCCC.C(OCC)C>CO>[CH:1]1([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 160 °C

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 1748 cm-1 ; NMR (CDCl3) δ1.33 (m, 23H), 1.54 (t, 2H, J=8 Hz), 2.31 (t, 2H, J=8 Hz), 3.66 (s, 3H). Anal. Calc'd. for C16H30O2 :C, 75.54; H, 11.89; Found: C, 75.67; H, 10.52.

Workup

temperature(ice bath cooling is applied when necessary to control exothermic excursions)
extractionis extracted with ethyl ether (3 times)
washThe combined ethereal extracts are washed with 2N hydrochloric acid
dry with materialare dried over magnesium sulfate
filtrationFiltration and evaporation
customgives an oily solid
washas eluting solvent

Sources & evidence

ORD record: ord-9be29920dad44f26b607f2286368c240
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05366993

Reaction notes

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