Hydrogen Peroxide → 4-Phenyl-2-indanone

HRID 67815Notes

Reaction equation

HRID 67815 reaction equation
[OH:1]O.[C:3]1([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:17]=2[CH2:16][CH:15]=[CH:14]3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)=O>[C:3]1([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:17]=2[CH2:16][C:15](=[O:1])[CH2:14]3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 129423867-Phenyl-1H-indene

Product 1

HCID 129423874-Phenyl-2-indanone

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A stirred solution of 53.2 ml of formic acid and 10.5 ml of 30% hydrogen peroxide was heated to 35° C., and 14.5 g (0.075 mole) of 7-phenyl-1H-indene was added dropwise causing the reaction mixture temperature to rise to 41° C. Upon complete addition the reaction mixture was allowed to cool to ambient temperature and was stirred for 16 hours. The reaction mixture was concentrated under reduced pressure to give a residual semi-solid which was subjected to steam distillation in the presence of aqueous dilute sulfuric acid. The steam distillates were filtered to give 1.84 g of 4-phenyl-2-indanone; m.p. 133°-136° C. The nmr and the ir spectra were consistent with the proposed structure.

Workup

  1. customto rise to 41° C
  2. additionUpon complete addition the reaction mixture
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customto give a residual semi-solid which
  5. distillationwas subjected to steam distillation in the presence of aqueous dilute sulfuric acid
  6. filtrationThe steam distillates were filtered

Sources & evidence

ORD record
ord-976497c06569439687ed8ce7dbded4ef
Source dataset
uspto-grants-1982_08
Patent number
US04346251

Reaction notes

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