Carbon Dioxide → 7-Cyclopropylheptanoic acid

HRID 1730815Notes

Reaction equation

HRID 1730815 reaction equation
[Mg].BrCCBr.Br[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:15][CH2:14]1.[C:16](=[O:18])=[O:17]>O1CCCC1>[CH:13]1([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:16]([OH:18])=[O:17])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 78391,2-Dibromoethane2×HCID 5462224MagnesiumHCID 22413033(6-Bromohexyl)cyclopropane

Product 1

HCID 161141377-Cyclopropylheptanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.684 g. Magnesium metal is covered with 2 ml. anhydrous tetrahydrofuran and 0.2 ml. 1,2-dibromoethane is added with stirring and heating. 1-Bromo-6-cyclopropylhexane (4.8 g.) and tetrahydrofuran (25 ml.) are added portionwise. An additional 0.207 ml. of 1,2-dibromethane is added and the reaction mixture refluxed for 3 hours. The solution is then maintained at 24°-28° while anhydrous carbon dioxide is bubbled through it for 11/2 hours. After stirring overnight under carbon dioxide, dry ether, water and 2N sulfuric acid are added until the pH is less than 7. The solution is extracted with ether and washed with water and brine, dried over calcium sulfate, filtered and the solvent removed to yield 7-cyclopropylheptanoic acid.

Workup

  1. temperatureheating
  2. temperaturethe reaction mixture refluxed for 3 hours
  3. customis bubbled through it for 11/2 hours
  4. stirringAfter stirring overnight under carbon dioxide
  5. additiondry ether, water and 2N sulfuric acid are added until the pH is less than 7
  6. extractionThe solution is extracted with ether
  7. washwashed with water and brine
  8. dry with materialdried over calcium sulfate
  9. filtrationfiltered
  10. customthe solvent removed

Sources & evidence

ORD record
ord-c35bae9fc88043dd89c0afcbe366d5c9
Source dataset
uspto-grants-1976_11
Patent number
US03993773

Reaction notes

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