Hydrochloric Acid → HCID 20327364, compound

HRID 372608Notes

Reaction equation

HRID 372608 reaction equation
[CH3:1][C:2]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4]([CH3:10])([CH3:9])[CH:3]2[CH:11]=[CH:12][C:13](=[O:15])[CH3:14].[C:16]12([CH3:26])[C:23]([CH3:25])([CH3:24])[CH:20]([CH2:21][CH2:22]1)[CH2:19][C:17]2=O.[OH-].[K+].Cl>CO>[CH3:26][C:16]12[C:23]([CH3:25])([CH3:24])[CH:20]([CH2:21][CH2:22]1)[CH2:19][CH:17]2[CH2:14][C:13](=[O:15])[CH2:12][CH2:11][CH:3]1[C:4]([CH3:9])([CH3:10])[CH:5]2[CH2:8][C:2]1([CH3:1])[CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2537CamphorHCID 14797Potassium HydroxideHCID 70618819HCID 70618819, compound

Product 1

HCID 20327364HCID 20327364, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
20 °C

Procedure

20.6 gm. (0.1 mole) of 1-(1,3,3-trimethylbicyclo-[2.2.1]hept-2-yl)-1-buten-3-one and 18.3 gm. (0.12 mole) of camphor is dissolved in 25 ml. methyl alcohol. A solution of 3.4 gm. of potassium hydroxide in 20 ml. of methyl alcohol is then added over a period of 15 minutes using good agitation and external cooling. The reaction mixture is maintained at 40°-45° C. for 6 hours, cooled to 20° C., made slightly acid by the addition of dilute hydrochloric acid and the residue after solvent stripping under reduced pressure extracted with ether. The ether solution is washed two times with one-tenth its volume of cold water, dried over anhydrous magnesium sulfate and stripped of solvent under reduced pressure. The residual oil which contained 1-(1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene)-4-(1,3,3-trimethylbicyclo[2.2.1]hept-2-yl)but-3-en-2-one is dissolved in 100 ml. of thiophene-free benzene and shaken under 50 psi hydrogen pressure in the presence of 3 gm. 5% palladium on carbon at 25° C. until slightly more than theoretical hydrogen uptake is observed. The catalyst is removed by filtration and the solvent stripped. The residual oil is purified by fractional distillation under reduced pressure to provide the 1-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)-4-(1,3,3-trimethylbicyclo[2.2.1]hept-2-yl)butan-2-one.

Workup

  1. temperatureThe reaction mixture is maintained at 40°-45° C. for 6 hours
  2. extractionthe residue after solvent stripping under reduced pressure extracted with ether
  3. washThe ether solution is washed two times with one-tenth its volume of cold water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. dissolutionis dissolved in 100 ml
  6. customat 25° C.
  7. customThe catalyst is removed by filtration
  8. distillationThe residual oil is purified by fractional distillation under reduced pressure

Sources & evidence

ORD record
ord-2a3d9ad4e531430b8a8bd16d35e9ca55
Source dataset
uspto-grants-1978_05
Patent number
US04091020

Reaction notes

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