2-Naphthalenebutanoic acid → 2,3-Dihydro-1H-phenanthren-4-one

HRID 329350Notes

Reaction equation

HRID 329350 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O>CS(O)(=O)=O>[CH2:11]1[C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:1]=2[C:14](=[O:16])[CH2:13][CH2:12]1

Participants

3

Reactant 1

HCID 2203952-Naphthalenebutanoic acid

Product 1

HCID 2404612,3-Dihydro-1H-phenanthren-4-oneYield 73.8%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

To 300 ml of methane-sulfonic acid contained in a 1 liter, 3-neck flask equipped with thermometer, drying tube and magnetic stirring bar was added 82.0 g (0.38 mole) of γ-(2-naphthyl)butyric acid as prepared above and the reaction mixture was heated at 90°-95° C. for one hour with vigorous stirring. The yellow reaction mixture was cooled, poured on crushed ice and extracted with two 350 ml portions of ethyl acetate. The combined organic portions were washed with 5% aqueous sodium hydroxide, water, dried over anhydrous sodium sulfate and then treated with some silica gel powder and Norit A charcoal before filtering. Upon removing the solvent an off-white solid was obtained. Recrystallization from 375 ml of hexane containing 7-10 ml of chloroform gave an oil that solidified to yield 55.0 g (73.3% by weight) of 1,2,3,4-tetrahydro-4-phenanthrone as an off-white solid. M.P. 64°-66° C.; λmax 312 nm (7,510) ethanol; T.L.C. CH2Cl2. Rf =.7.

Workup

  1. customequipped with thermometer
  2. customdrying tube and magnetic stirring bar
  3. customas prepared above and the reaction mixture
  4. temperaturewas heated at 90°-95° C. for one hour with vigorous stirring
  5. temperatureThe yellow reaction mixture was cooled
  6. additionpoured
  7. customon crushed ice
  8. extractionextracted with two 350 ml portions of ethyl acetate
  9. washThe combined organic portions were washed with 5% aqueous sodium hydroxide, water
  10. dry with materialdried over anhydrous sodium sulfate
  11. additiontreated with some silica gel powder and Norit A charcoal
  12. filtrationbefore filtering
  13. customUpon removing the solvent an off-white solid
  14. customwas obtained
  15. customRecrystallization from 375 ml of hexane containing 7-10 ml of chloroform
  16. customgave an oil that

Sources & evidence

ORD record
ord-5d1aae53dd9f4f43b00b5da793249f1a
Source dataset
uspto-grants-1990_01
Patent number
US04891298

Reaction notes

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