Nitromethane → HCID 54034481, compound

HRID 1196261Notes

Reaction equation

HRID 1196261 reaction equation
[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[C:13]1([C:19]2([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:24][CH2:23][C:22](=[O:25])[CH:21]=[CH:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[N+:32]([CH3:35])([O-:34])=[O:33]>CO.CC(O)(C)C.O1CCCC1>[N+:32]([CH2:35][CH:20]1[C:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:24][CH2:23][C:22](=[O:25])[CH2:21]1)([O-:34])=[O:33]

Participants

7

Reactant 3

HCID 6375NitromethaneHCID 66854Benzyltrimethylammonium hydroxideHCID 1382802-Cyclohexen-1-one, 4,4-diphenyl-

Product 1

HCID 54034481HCID 54034481, compoundYield 92.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution (11.45 g) of benzyltrimethylammonium hydroxide in methanol is added to a solution of 4,4-diphenyl-2-cyclohexenone (60 g) and nitromethane (14.75 g) in 2-methyl-2-propanol (400 cc) and anhydrous tetrahydrofuran (200 cc), and the reaction mixture is stirred at +25° C. for 144 hours: a crystalline solid precipitates slowly. This suspension is filtered and the crystals are washed with petroleum ether (50 cc) cooled to 0° C., drained and dried. (RS)-3-Nitromethyl-4,4-diphenylcyclohexanone (69.1 g) is obtained in the form of white crystals, m.p. 164° C.

Workup

  1. customa crystalline solid precipitates slowly
  2. filtrationThis suspension is filtered
  3. washthe crystals are washed with petroleum ether (50 cc)
  4. customdried

Sources & evidence

ORD record
ord-93fe803800c14c34ba74e60ab96bcbad
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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