Methyl nitrite → 1,1-Dimethoxy-2-nitrosocyclopentane

HRID 1706118Notes

Reaction equation

HRID 1706118 reaction equation
COC1CCCC=1.CON=O.[CH3:12][O:13][C:14]1([O:21][CH3:22])[CH2:18][CH2:17][CH2:16][C:15]1=[N:19][OH:20]>OS(O)(=O)=O.O=S(=O)=O>[CH3:22][O:21][C:14]1([O:13][CH3:12])[CH2:18][CH2:17][CH2:16][CH:15]1[N:19]=[O:20]

Participants

5

Reactant 3

HCID 12231Methyl nitriteHCID 1368351-MethoxycyclopenteneHCID 867350411,1-Dimethoxy-2-oximinocyclopentane

Product 1

HCID 542746821,1-Dimethoxy-2-nitrosocyclopentane

Reagents, catalysts & solvents 1

HCID 24681Fuming sulfuric acidCatalyst

Procedure

1,1-Dimethoxy-2-nitrosocyclopentane dimer was prepared as in Example 1 by reacting 1-methoxycyclopentene (15.9 g., 0.162 mole) with an excess of methylnitrite (29.7 g., 0.48 mole) using 0.5 mole percent of 20% oleum as catalyst. The product (20.5 g.) was mostly the desired dimer with a small amount of 1,1-dimethoxy-2-oximinocyclopentane. An additional 5 grams of product were recovered by flash evaporation of the wash liquors. The structure was confirmed by IR and nmr.

Workup

  1. customAn additional 5 grams of product were recovered by flash evaporation of the wash liquors

Sources & evidence

ORD record
ord-63d68a48028f4205bc043ca32d4360eb
Source dataset
uspto-grants-1980_06
Patent number
US04206112

Reaction notes

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