Water → 3-methylthio-5H-dibenzo[a,d]cyclohepten-5-ol

HRID 2290287Notes

Reaction equation

HRID 2290287 reaction equation
[BH4-].[Na+].[CH3:3][S:4][C:5]1[CH:6]=[CH:7][C:8]2[CH:14]=[CH:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[C:10](=[O:19])[C:9]=2[CH:20]=1.O>C(O)C.[OH-].[Na+]>[CH3:3][S:4][C:5]1[CH:6]=[CH:7][C:8]2[CH:14]=[CH:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[CH:10]([OH:19])[C:9]=2[CH:20]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 202322193-methylthio-5H-dibenzo[a,d]cyclohepten-5-one

Product 1

HCID 202322443-methylthio-5H-dibenzo[a,d]cyclohepten-5-ol

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 702EthanolSolvent

Procedure

In operations carried out in a manner similar to that described in Example VI, 0.5 gram (13 millimoles) of sodium borohydride was added to a solution of 0.8 gram (3.2 millimoles) of 3-methylthio-5H-dibenzo[a,d]cyclohepten-5-one in 20 milliliters of ethanol to which 1 drop of 40 percent sodium hydroxide had been added and the resulting mixture stirred overnight at room temperature. Thereafter, water was added to the reaction mixture, the aqueous mixture subjected to reduced pressure to remove the ethanol, the remaining aqueous solution extracted with ether, the ether solution washed successively with water and saturated sodium chloride, and then dried over magnesium sulfate. The dried solution was subjected to reduced pressure to obtain the 3-methylthio-5H-dibenzo[a,d]cyclohepten-5-ol intermediate as a white solid.

Workup

  1. additionhad been added
  2. customto remove the ethanol
  3. extractionthe remaining aqueous solution extracted with ether
  4. washthe ether solution washed successively with water and saturated sodium chloride
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-c2aeacbfab4c4d729d65c7d95a8afc6a
Source dataset
uspto-grants-1986_10
Patent number
US04616023

Reaction notes

Loading…