Hydrochloric Acid → 1,4a-Dimethyl-4,4a,9,10-tetrahydrophenanthren-2(3H)-one

HRID 1639286Notes

Reaction equation

HRID 1639286 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]([CH2:19][CH3:20])=[O:18])=[CH2:16].Cl>CO>[CH3:16][C:15]1[C:17](=[O:18])[CH2:19][CH2:20][C:4]2([CH3:3])[C:5]=1[CH2:6][CH2:7][C:8]1[C:13]2=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 153941-Penten-3-oneHCID 982091-Methyl-3,4-dihydro-1H-naphthalen-2-one

Product 1

HCID 146763031,4a-Dimethyl-4,4a,9,10-tetrahydrophenanthren-2(3H)-oneYield 103.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
-15 °C

Procedure

Potassium hydroxide in the amount of 2.24 g (40 mmol) was dissolved in 50 ml of 90 % methanol 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 5.17 g (32 mmol) of 1-methyl-2-tetralone was added dropwisely to the above obtained solution over a period of 10 minutes. The reaction vessel was then cooled to -15° C., and 2.67 g (31 mmol) of ethyl vinyl ketone was added dropwisely to the reaction vessel. The temperature of the resulted mixture was brought to room temperature over a period of 4 hours under agitation in a stream of nitrogen gas. The mixture had been allowed to stand over night, and then the mixture was refluxed under heating for 3 hours in an atmosphere of nitrogen gas. After the temperature of the mixture had been brought to room temperature, the mixture was made acidic with hydrochloric acid and then 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 7.27 g of oily yellow residue. This residue was allowed to stand to obtain 5.54 g of crystals. These crystals were recrystallized twice from cyclohexane to obtain 3.95 g of colorless needle-like crystals.

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 over a period of 10 minutes
  3. waitto stand over night
  4. temperaturethe mixture was refluxed
  5. temperatureunder heating for 3 hours in an atmosphere of nitrogen gas
  6. customhad been brought to room temperature
  7. extractionextracted with ether
  8. customThe ether layer was removed
  9. washwashed with water
  10. dry with materialdried with sodium sulfate
  11. distillationThe ether was distilled off

Sources & evidence

ORD record
ord-fea864dc190b41e18cdb75fa452b3b1b
Source dataset
uspto-grants-1989_11
Patent number
US04883822

Reaction notes

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