Sodium Hydroxide → Benzonorbornadienone

HRID 1534429Notes

Reaction equation

HRID 1534429 reaction equation
[C:1]12[CH2:7][C:4](=[CH:5][CH:6]=1)[C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][C:2]2=1.[OH-:12].[Na+].[BH4-].[Na+]>O.O1CCCC1>[C:4]12[C:5](=[O:12])[CH:6]=[C:1]([CH:7]=1)[C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]2=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 566125711,4-Methanonaphthalene

Product 1

HCID 129692535Benzonorbornadienone

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of mercuric acetate (4 g) in water (10 ml) was treated with a solution of benzobicyclo[2.2.1]heptadiene (2 g) in tetrahydrofuran (25 ml) and the resulting mixture was stirred at room temperature for 24 hours. The solution was treated with a solution of 10% sodium hydroxide in water (5 ml), followed by sodium borohydride (0.5 g). The resulting mixture was stirred for 30 minutes and the resulting layers were separated. The aqueous layer was extracted with ether (2×30 ml) and the combined organic layers were dried over magnesium sulfate and concentrated on a rotary evaporator. The residue was combined with methylene chloride (25 ml) and pyridinium chlorochromate (3 g) and the solution was stirred at room temperature for 12 hours. The solution was washed with water (30 ml) and the organic layer was dried over magnesium sulfate. The solvent was removed on a rotary evaporator and the product was purified by preparative centrifugally accelerated radial thin layer chromatography using 25% ethyl acetate in hexane as the eluant. After removal of the eluant on a rotary evaporator, the product was obtained as a yellow oil.

Workup

  1. stirringThe resulting mixture was stirred for 30 minutes
  2. customthe resulting layers were separated
  3. extractionThe aqueous layer was extracted with ether (2×30 ml)
  4. dry with materialthe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated on a rotary evaporator
  6. stirringthe solution was stirred at room temperature for 12 hours
  7. washThe solution was washed with water (30 ml)
  8. dry with materialthe organic layer was dried over magnesium sulfate
  9. customThe solvent was removed on a rotary evaporator
  10. customthe product was purified by preparative centrifugally accelerated radial thin layer chromatography
  11. customAfter removal of the eluant
  12. customon a rotary evaporator
  13. customthe product was obtained as a yellow oil

Sources & evidence

ORD record
ord-d4ed203921c14fd6b0005de9ed37c05d
Source dataset
uspto-grants-1992_02
Patent number
US05089506

Reaction notes

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