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

HRID 1580280Notes

Reaction equation

HRID 1580280 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(OCC)=C>[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

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8023Ethyl vinyl etherSolvent

Procedure

15.8 g (0.1 mol) of 5-isopropoxy-3-methyl-1-penten-3-ol and 20.0 g of mercuric acetate in 180 cc of ethyl vinyl ether are maintained at reflux temperature over the course of 4 days. 0.9 cc of glacial acetic acid is added at 20° to the turbid solution. After 3 hours 150 cc of 5% potassium carbonate solution are added and the product is extracted with hexane. The hexane extract is dried with sodium sulphate and evaporated. The residue is heated to 165°-168° over the course of 11/2 hours without further purification and in an atmosphere of nitrogen; the residue is subsequently distilled at reduced pressure. The 7-isopropoxy-5-methyl-4-heptenal has a B.P. of 70°-73°/0.8 mm.

Workup

  1. temperatureat reflux temperature over the course of 4 days
  2. extractionthe product is extracted with hexane
  3. extractionThe hexane extract
  4. dry with materialis dried with sodium sulphate
  5. customevaporated
  6. temperatureThe residue is heated to 165°-168° over the course of 11/2 hours without further purification and in an atmosphere of nitrogen
  7. distillationthe residue is subsequently distilled at reduced pressure

Sources & evidence

ORD record
ord-57bb350cc7b24fe2aa5c2b0ec2d2f586
Source dataset
uspto-grants-1976_01
Patent number
US03932483

Reaction notes

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