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

HRID 2071744Notes

Reaction equation

HRID 2071744 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[C:8](=[O:17])[C:7]=2[CH:18]=1.CO.[BH4-].[K+].[OH-].[Na+]>O>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[CH:8]([OH:17])[C:7]=2[CH:18]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 4192641Potassium 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 1

HCID 962WaterSolvent

Procedure

3-Methylmercapto-5H-dibenzo[a,d]cyclohepten-5-one, 2.9 g. (0.11 mole), is dissolved in 500 ml. of methanol. The solution is stirred and heated to refluxing while a solution of 14.9 g. (0.276 mole) of potassium borohydride in 150 ml. of water containing 0.2 ml. of 10 N. sodium hydroxide is added dropwise. After stirring at reflux for 2 hours, the solution is chilled and the precipitated product collected and washed with methanol yielding, typically, 27 g. (96%). An analytical sample melts at 117°-118.5° C. after repeated recrystallizations from methanol.

Workup

  1. dissolution(0.11 mole), is dissolved in 500 ml
  2. temperatureheated
  3. temperatureto refluxing while a solution of 14.9 g
  4. stirringAfter stirring
  5. temperatureat reflux for 2 hours
  6. temperaturethe solution is chilled
  7. customthe precipitated product collected
  8. washwashed with methanol yielding
  9. customrecrystallizations from methanol

Sources & evidence

ORD record
ord-8b75b4de51c9490aa3dc2e6752ac649a
Source dataset
uspto-grants-1977_09
Patent number
US04048223

Reaction notes

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