Hydrochloric Acid → 2(3H)-Phenanthrenone, 4,4a,9,10-tetrahydro-4a-methyl-

HRID 1639287Notes

Reaction equation

HRID 1639287 reaction equation
[OH-].[K+].[CH3:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][C:5]1=O.[CH:15]([C:17]([CH3:19])=[O:18])=[CH2:16].Cl>O.CO>[CH3:3][C:4]12[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][CH2:6][C:5]1=[CH:19][C:17](=[O:18])[CH2:15][CH2:16]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6570Methyl vinyl ketoneHCID 14797Potassium HydroxideHCID 982091-Methyl-3,4-dihydro-1H-naphthalen-2-one

Product 1

HCID 6075872(3H)-Phenanthrenone, 4,4a,9,10-tetrahydro-4a-methyl-Yield 90.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
-15 °C

Procedure

Potassium hydroxide in the amount of 2.25 g (40 mmol) was dissolved in 4.5 g of water in 100-ml three-necked flask, and the obtained solution was then cooled with ice under agitation in a stream of nitrogen gas. A methanol solution (8 ml) containing 4.8 g (30 mmol) of 1-methyl-2-tetralone was added dropwisely to the above obtained solution. The reaction vessel was cooled to -15° C., then, 2.1 g (30 mmol) of methyl vinyl ketone was added dropwisely to the reaction vessel and 2 ml of methanol was further added thereto. The resulted mixture was agitated under cooling with ice for 1 hour and then at room temperature for 6 hours in a stream of nitrogen-gas. Then, the mixture had been allowed to react at 70° C. for 6 hours. The reaction mixture was then poured into iced water, made acidic with hydrochloric acid and extracted with ether. The ether layer was removed and washed with water, and then dried with sodium sulfate. The ether was distilled off to obtain 5.75 g of oily yellowish orange residue. A part of this residue was crystallized and resulted crystals were recrystallized twice from cyclohexane to obtain 2.8 g of colorless plate-like crystals. The oily portion was further allowed to crystallize to obtain 1.9 g of crystals. The total yield was 4.7 g.

Workup

  1. temperaturethe obtained solution was then cooled with ice under agitation in a stream of nitrogen gas
  2. additionwas added dropwisely to the above obtained solution
  3. additionwas further added
  4. temperatureunder cooling with ice for 1 hour
  5. customto react at 70° C. for 6 hours
  6. extractionextracted with ether
  7. customThe ether layer was removed
  8. washwashed with water
  9. dry with materialdried with sodium sulfate
  10. distillationThe ether was distilled off

Sources & evidence

ORD record
ord-039428fac578444aa250f90898119247
Source dataset
uspto-grants-1989_11
Patent number
US04883822

Reaction notes

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