Carbon Dioxide → 13-Methyltetradecanoic acid

HRID 1872806Notes

Reaction equation

HRID 1872806 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15].[C:17](=[O:19])=[O:18].Cl>O1CCCC1.C(OCC)(=O)C>[CH3:15][CH:14]([CH3:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:17]([OH:19])=[O:18]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 110657331-Bromo-12-methyltridecane

Product 1

HCID 15101413-Methyltetradecanoic acidYield 57.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Magnesium (1.5 g) was added to a solution of 1-bromo-12-methyltridecane (15.0 g) in tetrahydrofuran (200 ml). The mixture was refluxed for 10 minutes under nitrogen atmosphere and stirred for 1 hour at room temperature. A solid of carbon dioxide (50 g) was added to the mixture. To the mixture was added a mixture of 1% hydrochloric acid (300 ml) and ethyl acetate (150 ml). The organic layer was washed with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on a silica gel column eluting with chloroform to give 13-methyltetradecanoic acid as an oil (7.54 g).

Workup

  1. temperatureThe mixture was refluxed for 10 minutes under nitrogen atmosphere
  2. additionTo the mixture was added
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on a silica gel column
  7. washeluting with chloroform

Sources & evidence

ORD record
ord-92bc3fe3dd68485fabfdb41338a743c4
Source dataset
uspto-grants-2000_08
Patent number
US06110933

Reaction notes

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