Pyridine → HCID 13561793, compound

HRID 1380372Notes

Reaction equation

[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:14][CH2:15][C:16](=[O:18])[CH3:17].N1C=CC=CC=1.[Mn]([O-])(=O)(=O)=[O:26].[K+]>O>[O:26]=[C:12]1[C:13]2[CH:1]=[C:2]([CH2:14][CH2:15][C:16](=[O:18])[CH3:17])[CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

Conditions

Temperature: 60 °C

Procedure

4-(2-Fluorenyl)-butan-2-one (4.72grams) was dissolvedin a mixture of 60 ml of pyridine and 5 ml of water, the mixture was heated at 60° C., and stirred. Potassium permanganate (6.8 grams) was added thereto little by little during 2 hours. When the addition was finished, the mixture was stirred for 2 hours more. The reaction solution was filtered, the filtrate was concentrated, and the resulting residue was dissolved in chlroform, the solution was washed with in the order of 10% hydrochloric acid, water, saturated sodium bicarbonate, and water, then dried with magensium sulfate, the solvent was evaporated therefrom, and the residue was recrystallized from ethanol to give 1.3 grams of 4-(9-oxo-2fluorenyl)-butan-2-one, yellow crystals, m.p. 75°-77° C.

Workup

additionWhen the addition
stirringthe mixture was stirred for 2 hours more
filtrationThe reaction solution was filtered
concentrationthe filtrate was concentrated
dissolutionthe resulting residue was dissolved in chlroform
washthe solution was washed with in the order of 10% hydrochloric acid, water, saturated sodium bicarbonate, and water
dry with materialdried with magensium sulfate
customthe solvent was evaporated
customthe residue was recrystallized from ethanol

Sources & evidence

ORD record: ord-741e27b163b8441c80149bd380c0cd2b
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04581377

Reaction notes

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