Aluminum → HCID 19901996, compound

HRID 1449321Notes

Reaction equation

HRID 1449321 reaction equation
[Al].[CH3:2][C:3]1[CH2:8][C:7]([CH3:10])([CH3:9])[CH:6]([C:11](=[O:13])[CH3:12])[CH2:5][CH:4]=1>[Al].C(O)(CC)C>[CH3:2][C:3]1[CH2:8][C:7]([CH3:9])([CH3:10])[CH:6]([CH:11]([OH:13])[CH3:12])[CH2:5][CH:4]=1

Participants

5

Reactant 2

HCID 5359268Aluminum2×HCID 205472391-(4,6,6-Trimethylcyclohex-3-en-1-yl)ethan-1-one

Product 1

HCID 19901996HCID 19901996, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 5359268AluminumCatalystHCID 6568(+-)-2-ButanolSolvent2×

Procedure

9.6 g of aluminium, 2.8 g of aluminium isopropylate, 0.2 g of mercuric chloride and 130 g of secondary butyl alcohol are introduced into a flask and the mixture is brought to reflux. Once the aluminium has started to react, 390 g of secondary butyl alcohol are slowly added over 45 minutes, maintaining reflux. Heating is then dicontinued and the mixture is left to attain the ambient temperature, stirring is discontinued and a calcium chloride drying tube is fitted. The mixture in then left overnight. On the following day, the mixture is brought to reflux and 332 g of 1,5,5-trimethyl-4-acetyl-cyclohex-1-ene are added in the course of about 2 hours. When the vapour temperature reaches 80°, the methyl ethyl ketone formed starts to distill off; the duration of the distillation is about 6 hours--finally under a pressure of 50 mm of mercury. The residue is taken up in 500 ml of benzene and washed twice with 100 ml of 10% sulphuric acid, twice with 100 ml of water, twice with 100 ml of a sodium bicarbonate solution and then with water until neutral. Distillation of the solvent over a water bath under reduced pressure gives 322 g of crude product, which are fractionated in a 500 ml three-necked flask fitted with a 1 meter adiabatic column having an unoxidisable filling with a particle size of 4×4 mm. 190.8 g of 1,5,5-trimethyl-4-(1-hydroxyethyl)-cyclohex-1-ene (57%) are obtained, having the following physical properties:

Workup

  1. temperatureto reflux
  2. customto react
  3. temperaturemaintaining
  4. temperaturereflux
  5. temperatureHeating
  6. waitthe mixture is left
  7. customthe ambient temperature
  8. customa calcium chloride drying tube is fitted
  9. temperatureto reflux
  10. customreaches 80°
  11. distillationthe methyl ethyl ketone formed starts to distill off
  12. distillationthe duration of the distillation
  13. waitis about 6 hours
  14. washwashed twice with 100 ml of 10% sulphuric acid, twice with 100 ml of water, twice with 100 ml of a sodium bicarbonate solution
  15. distillationDistillation of the solvent over a water bath under reduced pressure
  16. customgives 322 g of crude product, which
  17. customare fractionated in a 500 ml three-necked flask
  18. customfitted with a 1 meter adiabatic column

Sources & evidence

ORD record
ord-6a0f4fa2a8504bf78a80ee5100bd36e4
Source dataset
uspto-grants-1980_02
Patent number
US04190561

Reaction notes

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