Magnesium → 3-Cyclododecylpropanoic acid, methyl ester

HRID 37299Notes

Reaction equation

HRID 37299 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

5

Reactant 3

HCID 5462224MagnesiumHCID 21584099Diethylether hexaneHCID 54459867Methyl 3-cyclododecylprop-2-enoate

Product 1

HCID 152958663-Cyclododecylpropanoic acid, methyl esterYield 61.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 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).

Workup

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

Sources & evidence

ORD record
ord-e2c3ab7dfdda4ca6a0114dee978d2e42
Source dataset
uspto-grants-1995_05
Patent number
US05420153

Reaction notes

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