Hydrochloric Acid → (E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one

HRID 1633177Notes

Reaction equation

HRID 1633177 reaction equation
[CH3:1][C:2]1[CH:3]([C:10]([OH:17])(CC=C)[CH2:11][CH:12]=[CH2:13])[C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][CH:7]=1.CC(C)([O-])C.[K+].Cl>CN(C)C=O>[CH3:13]/[CH:12]=[CH:11]/[C:10]([CH:3]1[C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][CH:7]=[C:2]1[CH3:1])=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 13894195HCID 13894195, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 5366077(E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 g of 2,6,6-trimethyl-1-[4-hydroxy-hepta-1,6-dien-4-yl]-cyclohex-2-ene have been added at room temperature and under stirring to a solution of 80 g of potassium tert-butoxide in 180 ml of dimethylformamide, while the temperature raised to 60°. After having been left at this temperature for 6 min., the mixture is put into an aqueous HCl solution (150 ml of conc. HCl/200 ml H2O). A vapour phase distillation has given 4 l of distillate which was then extracted with petrol ether (80°-100°). After the usual treatments of separation, drying and evaporation of the organic extracts, 71 g of a mixture of iso- α-damascone and α-damascone were obtained.

Workup

  1. temperatureraised to 60°
  2. distillationA vapour phase distillation
  3. extractionwas then extracted with petrol ether (80°-100°)
  4. customAfter the usual treatments of separation
  5. customdrying
  6. customevaporation of the organic extracts, 71 g of a mixture of iso- α-damascone

Sources & evidence

ORD record
ord-527350443fb7451583e8a298f776f300
Source dataset
uspto-grants-1984_10
Patent number
US04479011

Reaction notes

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