Water → Dibenzosuberenol

HRID 344813

Reaction equation

HRID 344813 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].O>C(O)(C)C>[CH:12]1[C:8]2[CH:9]=[CH:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH:6]([OH:16])[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 166795H-Dibenzo[a,d]cyclohepten-5-oneHCID 4311764Sodium borohydride

Product 1

HCID 82577DibenzosuberenolYield 98%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5H-Dibenzo[a,d]cyclohepten-5-one (10 g) is dissolved in 80 ml of isopropyl alcohol and sodium borohydride (1.8 g) is added at once. The mixture is stirred at room temperature for two hr. 5 ml of water are added to quench the reaction and the solvent is evaporated. The residue is taken up in diethyl ether and washed with water, dried over MgSO4 and evaporated. (9.8 g 98% yield) of 5H-dibenzo-[a,d]-cyclohepten-5-ol is obtained.

Workup

  1. customto quench
  2. customthe reaction
  3. customthe solvent is evaporated
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-df267eba836a431eaa272c9047342d2a
Source dataset
uspto-grants-1991_10
Patent number
US05053521

Linked notes

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