Hydrogen Peroxide → 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propan-1-ol

HRID 596534Notes

Reaction equation

HRID 596534 reaction equation
B.C([C:5]1[CH:20]=[CH:19][C:8]2[C:9](=[O:18])[C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[CH:12]=[CH:13][C:7]=2[CH:6]=1)C=C.[OH-].[Na+].OO.[O:25]1C[CH2:28][CH2:27][CH2:26]1>CCOCC.O>[CH:6]1[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]=[CH:20][C:5]=1[CH:27]([CH3:28])[CH2:26][OH:25]

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21449999HCID 21449999, compound

Product 1

HCID 214093932-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propan-1-olYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

1.67 Ml. of 1.0 molar borane in tetrahydrofuran is added to an ice-cooled solution of 1.23 gm. of 2-(2-propenyl) 5H-dibenzo[a,d]cyclohepten-5-one in 10 ml. of tetrahydrofuran. The mixture is stirred for 2 hours and then 5 ml. of 3.0 molar aqueous sodium hydroxide and 1.5 ml. of 30% hydrogen peroxide are added. The reaction is left for one hour and then water and ether are added. The ethereal layer is washed, dried and evaporated. The product is chromatographed on 50 gm. silica gel, eluting with 1:1 ether/hexane, so as to obtain a 50% yield of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propan-1-ol, m.p. (hexane) 63°-66° C.

Workup

  1. temperaturecooled solution of 1.23 gm
  2. waitThe reaction is left for one hour
  3. washThe ethereal layer is washed
  4. customdried
  5. customevaporated
  6. customThe product is chromatographed on 50 gm
  7. washsilica gel, eluting with 1:1 ether/hexane

Sources & evidence

ORD record
ord-59ecc0c9da2a48ce90c7335c3a134fc0
Source dataset
uspto-grants-1977_03
Patent number
US04011243

Reaction notes

Loading…