Acetic Acid → 7-Isopropoxy-5-methyl-4-heptenal

HRID 1580747Notes

Reaction equation

HRID 1580747 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][C:7]([CH3:11])(O)[CH:8]=[CH2:9])([CH3:3])[CH3:2].[C:12](O)(=[O:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>C(OC=C)C.C([O-])(=O)C.[Hg+]>[CH:1]([O:4][CH2:5][CH2:6][C:7]([CH3:11])=[CH:8][CH2:9][CH2:13][CH:12]=[O:14])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 23263480HCID 23263480, compound

Product 1

HCID 540432947-Isopropoxy-5-methyl-4-heptenal

Reagents, catalysts & solvents 2

HCID 61181Mercurous acetateCatalystHCID 8023Ethyl vinyl etherSolvent

Procedure

15.8 g (0.1 mol) of 5-isopropoxy-3-methyl-1-penten-3-ol (produced in accordance with Example 63) and 20.0 g of mercury acetate are kept in 180 cc of ethylvinyl ether at reflux temperature during the course of 4 days. 0.9 cc of glacial acetic acid is added at 20° to the solution which has rendered turbid. 150 cc of 5% potassium carbonate solution are added after 3 hours and the mixture is extracted with hexane. The hexane extract is evaporated and the residue is heated to 165°-168° during 11/2 hours in an atmosphere of nitrogen and without further purification; the residue is subsequently distilled at reduced pressure. B.P. of 7-isopropoxy-5-methyl-4-heptenal: 70°-73°/0.8 mm. nD20 = 1.4476

Workup

  1. temperatureat reflux temperature during the course of 4 days
  2. extractionthe mixture is extracted with hexane
  3. extractionThe hexane extract
  4. customis evaporated
  5. temperaturethe residue is heated to 165°-168° during 11/2 hours in an atmosphere of nitrogen
  6. customwithout further purification
  7. distillationthe residue is subsequently distilled at reduced pressure
  8. custom70°-73°/0.8 mm

Sources & evidence

ORD record
ord-a206865dee51418780f0e875f44cd156
Source dataset
uspto-grants-1976_01
Patent number
US03933804

Reaction notes

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