2-(2-Formylethyl)-3-isopropenyl-1-methyl-cyclopent-1-ene → 2-(2-Carboxyethyl)-3-isopropenyl-1-methyl-cyclopent-1-ene

HRID 1658177Notes

Reaction equation

HRID 1658177 reaction equation
[CH:1]([CH2:3][CH2:4][C:5]1[CH:9]([C:10]([CH3:12])=[CH2:11])[CH2:8][CH2:7][C:6]=1[CH3:13])=[O:2].CC(C)=[O:16].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:1]([CH2:3][CH2:4][C:5]1[CH:9]([C:10]([CH3:12])=[CH2:11])[CH2:8][CH2:7][C:6]=1[CH3:13])([OH:16])=[O:2]

Participants

4

Reactant 2

HCID 124807202-(2-Formylethyl)-3-isopropenyl-1-methyl-cyclopent-1-eneHCID 131709961Jones' reagent

Product 1

HCID 213885332-(2-Carboxyethyl)-3-isopropenyl-1-methyl-cyclopent-1-ene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 25 g of 2-(2-formylethyl)-3-isopropenyl-1-methyl-cyclopent-1-ene in 1200 ml of acetone was treated at -10°C with 55 ml of Jones reagent. The resulting brown mixture was poured on to ice/sodium bicarbonate solution. Ether extraction, washing neutral with sodium bicarbonate solution, saturated sodium chloride solution and water, drying of the extract with magnesium sulphate and removal of the solvent under reduced pressure yielded 20 g (80%) of a weakly yellow oily crude product from which there were obtained by distillation 15 g of pure 2-(2-carboxyethyl)-3-isopropenyl-1-methyl-cyclopent-1-ene; boiling point 0.01 = 102°C; IRfilm : μmax = 3600-2400, 1720, 1645, 1450, 1420, 1380, 1330, 1290, 1220, 1085, 945 and 900 cm-1. The compound has a woody, spicy, weakly sweetish and somewhat musty fragrance.

Workup

  1. extractionEther extraction
  2. washwashing neutral with sodium bicarbonate solution, saturated sodium chloride solution and water
  3. customdrying of the
  4. extractionextract with magnesium sulphate and removal of the solvent under reduced pressure
  5. customyielded 20 g (80%) of a weakly yellow oily crude product from which there

Sources & evidence

ORD record
ord-ea2f732f267a442db2fd51c3feb55dbb
Source dataset
uspto-grants-1976_06
Patent number
US03963675

Reaction notes

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