Nitric Acid → 8-Hydroxy-5-methyl-7-nitro-1,2,3,4,4a,9a-hexahydro-9-fluorenone

HRID 2051423Notes

Reaction equation

C(OC(=O)C)(=O)C.[N+:8]([O-:11])(O)=[O:9].[OH:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:27])=[C:17]2[C:25]=1[C:24](=[O:26])[CH:23]1[CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]1>C(O)(=O)C>[OH:12][C:13]1[C:14]([N+:8]([O-:11])=[O:9])=[CH:15][C:16]([CH3:27])=[C:17]2[C:25]=1[C:24](=[O:26])[CH:23]1[CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

Conditions

Temperature: 15 °C

Procedure

A mixture of 15 ml of acetic anhydride and 50 ml of acetic acid was ice-cooled and thereto was added dropwise 10 ml of nitric acid (d=1.38). After stirring for 1 hour, thereto was added dropwise an acetic acid solution containing 10 g of 8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone in 100 ml of acetic acid. After stirring for 30 minutes, the ice bath was removed and the solution was warmed to an inner temperature of 15° C. To this solution was added 150 ml of diethyl ether, followed by stirring under ice-cooling. The resulting precipitate was collected by filtration to obtain 8 g of 8-hydroxy-5-methyl-7-nitro-1,2,3,4,4a,9a-hexahydro-9-fluorenone of yellowish green powdery crystal.

Workup

temperaturecooled
stirringAfter stirring for 30 minutes
customthe ice bath was removed
additionTo this solution was added 150 ml of diethyl ether
stirringby stirring under ice-
temperaturecooling
filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record: ord-74b5425d67c34f8882c9ae699145cb6e
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05017724

Reaction notes

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