Dibenzosuberone → Dibenzosuberol

HRID 1981182Notes

Reaction equation

HRID 1981182 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][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.[OH-].[Na+]>[Zn].C(O)C>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([OH:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 14589DibenzosuberoneHCID 14798Sodium Hydroxide

Product 1

HCID 14588Dibenzosuberol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A mixture of 208 g of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one, 2 l of ethanol, 200 g of sodium hydroxide and 300 g of zinc powder is heated to boiling under reflux while stirring for 2 hours. The still warm mixture is filtered over kieselguhr while back-washing with about 1 l of methanol. After concentration of the yellow solution to about 1 l, the thick paste obtained is partitioned between 2 l of chloroform and 1 l of water. The alkaline-aqueous phase is adjusted to pH 3 to 4 with about 400 ml of concentrated hydrochloric acid while cooling with ice and extracted with 1 l of chloroform. The combined chloroform extracts are washed with water until they are neutral and subsequently dried over magnesium sulfate in the presence of a small amount of active carbon. After filtration and concentration of the clear, light yellowish solution, there is obtained 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol as an almost white, crystalline mass with a melting point of 89-91°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. filtrationThe still warm mixture is filtered over kieselguhr
  4. washwhile back-washing with about 1 l of methanol
  5. customAfter concentration of the yellow solution to about 1 l, the thick paste obtained
  6. customis partitioned between 2 l of chloroform and 1 l of water
  7. temperaturewhile cooling with ice
  8. extractionextracted with 1 l of chloroform
  9. washThe combined chloroform extracts are washed with water until they
  10. dry with materialsubsequently dried over magnesium sulfate in the presence of a small amount of active carbon
  11. filtrationAfter filtration and concentration of the clear, light yellowish solution

Sources & evidence

ORD record
ord-2e46e9c0bfe74cca8a0320bfaf9cc709
Source dataset
uspto-grants-1985_04
Patent number
US04513002

Reaction notes

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