Sodium Hydroxide → Dibenzosuberenol

HRID 1658639Notes

Reaction equation

HRID 1658639 reaction equation
[BH4-].[Na+].[OH-].[Na+].[CH:5]1[C:15]2[CH:14]=[CH:13][C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[C:10](=[O:20])[C:9]=2[CH:8]=[CH:7][CH:6]=1.[BH4-]>O.CO>[CH:16]1[C:12]2[CH:13]=[CH:14][C:15]3[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=3[CH:10]([OH:20])[C:11]=2[CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 166795H-Dibenzo[a,d]cyclohepten-5-oneHCID 28123BorohydrideHCID 4311764Sodium borohydride

Product 1

HCID 82577Dibenzosuberenol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent3×

Procedure

In this preparation a solution containing 1.5 grams of sodium borohydride in 30 ml. of water containing 1.5 ml. of 3N aqueous sodium hydroxide is added to a solution containing 15.0 g. of dibenzo[a,d]cyclohepten-5-one in 200 ml. of methanol at room temperature, with stirring. The resulting mixture is stirred for 45 minutes and then an additional 0.5 g. of borohydride in 10 ml. of water is added and the mixture stirred at room temperatue for 60 hours. The reaction mixture is then cooled in an ice water bath while 300 ml. of water is slowly added with stirring. The resulting precipitate is collected by filtration and washed repeatedly with water and dried under vacuum affording a residue of 5H-dibenzo[a,d]cyclohepten-5-ol, which is sufficiently pure to use as starting material for subsequent preparations.

Workup

  1. customIn this preparation a solution
  2. additioncontaining 15.0 g
  3. stirringthe mixture stirred at room temperatue for 60 hours
  4. temperatureThe reaction mixture is then cooled in an ice water bath while 300 ml
  5. stirringwith stirring
  6. filtrationThe resulting precipitate is collected by filtration
  7. washwashed repeatedly with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-a0cd1e6eeb1e4262a1e64c9065f468ec
Source dataset
uspto-grants-1976_06
Patent number
US03965181

Reaction notes

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