Nitromethane → Cyclohexanone, 3-(nitromethyl)-

HRID 1761745Notes

Reaction equation

HRID 1761745 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:8]([CH3:11])([O-:10])=[O:9].CCCCC=CCCC>C(O)(C)C>[N+:8]([CH2:11][CH:3]1[CH2:4][CH2:5][CH2:6][C:1](=[O:7])[CH2:2]1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 7967CyclohexanoneHCID 942264-Nonene

Product 1

HCID 10920766Cyclohexanone, 3-(nitromethyl)-Yield 100%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

21.9 g of cyclohexanone are left to stand together with 175 ml of nitromethane and 2.1 g of 5-diazabicyclo[4.3.0.]non-5-ene (DBN) in 250 ml of isopropanol at room temperature for 2 days. The working up is carried out in analogy to the procedure for Example 1 and provides 37.2 g (100% of theory) of 3-(nitromethyl)cyclohexanone which is pure enough for the next reaction. Rf =0.62 CH2Cl2 :CH3OH=99:1

Sources & evidence

ORD record
ord-f55e579a95334855ba8e938e15edb14b
Source dataset
uspto-grants-1989_05
Patent number
US04827032

Reaction notes

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