Ethyl vinyl ether → 2-(2-Formylethyl)-3-isopropenyl-1-methyl-cyclopent-1-ene

HRID 1658175Notes

Reaction equation

HRID 1658175 reaction equation
[C:1]([CH:4]1[CH2:8][CH2:7][C:6]([CH3:10])(O)[C:5]1=[CH2:11])([CH3:3])=[CH2:2].[CH:12]([O:14]CC)=[CH2:13]>P(=O)(O)(O)O>[CH:12]([CH2:13][CH2:11][C:5]1[CH:4]([C:1]([CH3:3])=[CH2:2])[CH2:8][CH2:7][C:6]=1[CH3:10])=[O:14]

Participants

4

Reactant 2

HCID 8023Ethyl vinyl etherHCID 30164943-Isopropenyl-1-methyl-2-methylenecyclopentan-1-ol

Product 1

HCID 124807202-(2-Formylethyl)-3-isopropenyl-1-methyl-cyclopent-1-eneYield 68.5%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidCatalyst

Procedure

12 drops of 85% phosphoric acid were added to a mixture, cooled to -15°C in a laboratory autoclave, of 76 g of 3-isopropenyl-1-methyl-2-methylene-cyclopentan-1-ol and 72 g of ethyl vinyl ether. After gassing with argon, the autoclave was brought, in an oil bath of 180°C, to an internal temperature of 150°C (this took about 15 minutes) and held at this temperature until a distinct drop in pressure occurred (about 100 minutes). The reaction mixture was then quenched, taken up in ether, washed with aqueous bicarbonate solution and water, the solution dried over anhydrous magnesium sulphate and concentrated under reduced pressure. The crude product (110 g), obtained as a yellow oil, was fractionated and yielded 61 g (68%) of pure 2-(2-formylethyl)-3-isopropenyl-1-methyl-cyclopent-1-ene having a woody, earthy fragrance; boiling point 0.2 = 64°-65°C; nD20 = 1.4888; IRfilm : μmax = 3080, 2725, 1725, 1642, 1440, 1370, 1060 and 895 cm-1.

Workup

  1. customthe autoclave was brought, in an oil bath of 180°C, to an internal temperature of 150°C
  2. customthis took about 15 minutes
  3. custom(about 100 minutes)
  4. customThe reaction mixture was then quenched
  5. washwashed with aqueous bicarbonate solution and water
  6. dry with materialthe solution dried over anhydrous magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product (110 g), obtained as a yellow oil

Sources & evidence

ORD record
ord-04e7147d167a4ff8b0e8ba863d975367
Source dataset
uspto-grants-1976_06
Patent number
US03963675

Reaction notes

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