Sodium borohydride → 3-chloro-5H-dibenzo[a,d]cyclohepten-5-ol

HRID 2290285Notes

Reaction equation

HRID 2290285 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[CH:13]=[CH:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[C:9](=[O:18])[C:8]=2[CH:19]=1>O.CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[CH:13]=[CH:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[CH:9]([OH:18])[C:8]=2[CH:19]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 126906103-Chloro-5H-dibenzo[A,D][7]annulen-5-one

Product 1

HCID 202322453-chloro-5H-dibenzo[a,d]cyclohepten-5-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 0.30 gram (0.0078 mole) of sodium borohydride in 5 milliliters of water was added to a solution of 0.75 gram (3.2 millimoles) of 3-chloro-5H-dibenzo[a,d]cyclohepten-5-one in 50 milliliters of methanol and the resulting mixture heated for 15 minutes at reflux temperature to obtain 3-chloro-5H-dibenzo[a,d]cyclohepten-5-ol intermediate in the reaction mixture. The solvent was evaporated and the residue intermediate slurried with water, filtered, washed and dried at 65° C. in vacuum oven for three hours.

Workup

  1. temperaturethe resulting mixture heated for 15 minutes
  2. temperatureat reflux temperature

Sources & evidence

ORD record
ord-edee3fb02bb346ba91292c6e312c7a20
Source dataset
uspto-grants-1986_10
Patent number
US04616023

Reaction notes

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