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

HRID 1834089Notes

Reaction equation

HRID 1834089 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 : νmax = 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-487585eb39a14e6a90c8121d48caff37
Source dataset
uspto-grants-1978_01
Patent number
US04068084

Reaction notes

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