Ethyl 1-propenyl ether → 2-(2-Formylpropyl)-3-isopropenyl-1-methyl-cyclopent-1-ene

HRID 1834091Notes

Reaction equation

HRID 1834091 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:15]CC)=[CH:13][CH3:14]>P(=O)(O)(O)O>[CH:12]([CH:13]([CH3:14])[CH2:11][C:5]1[CH:4]([C:1]([CH3:3])=[CH2:2])[CH2:8][CH2:7][C:6]=1[CH3:10])=[O:15]

Participants

4

Reactant 2

HCID 13570Ethyl 1-propenyl etherHCID 30164943-Isopropenyl-1-methyl-2-methylenecyclopentan-1-ol

Product 1

HCID 213885292-(2-Formylpropyl)-3-isopropenyl-1-methyl-cyclopent-1-eneYield 67%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidCatalyst

Procedure

15 drops of 85% phosphoric acid were added to a mixture, cooled to -30° C in a laboratory autoclave, of 76 g of 3-isopropenyl-1-methyl-2-methylene-cyclopentan-1-ol and 130 g of ethyl 1-propenyl ether. After gassing with nitrogen, 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 75 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 (135 g), obtained as a yellow oil, was fractionated and yielded 64 g (67%) of pure 2-(2-formylpropyl)-3-isopropenyl-1-methyl-cyclopent-1-ene having woody, earthy, musty fragrance; boiling point 0.005 = 51° C; nD20 = 1.4825; IRfilm : νmax = 3090, 2730, 1735, 1645, 1460, 1380 and 898 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 75 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 (135 g), obtained as a yellow oil

Sources & evidence

ORD record
ord-b7d0e948b21742cbaa3dba3132517048
Source dataset
uspto-grants-1978_01
Patent number
US04068084

Reaction notes

Loading…