Nitromethane → (1-Nitromethylcyclohexyl)acetic acid ethyl ester

HRID 1535024Notes

Reaction equation

HRID 1535024 reaction equation
[C:1]1(=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:13]([CH3:16])([O-:15])=[O:14].[OH-].[K+]>CS(C)=O>[N+:13]([CH2:16][C:1]1([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 14797Potassium HydroxideHCID 73776Ethyl cyclohexylideneacetate

Product 1

HCID 11128083(1-Nitromethylcyclohexyl)acetic acid ethyl esterYield 89.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

16.8 g (0.1 mole) Ethyl cyclohexylideneacetate, 9.2 g, (0.15 mole) nitromethane and 0.64 g (0.01 mole) potassium hydroxide (content 88%) in 40 mL dimethyl sulphoxide are stirred for 2 hours at 100° C. The reaction mixture is worked up analogously to Example 2 to give 20.5 g ethyl 1-nitromethyl-1-cyclohexaneacetate (89.4% of theory). According to GC., the content is 82.8% and 10.2% of starting compound and 4.1% of by-product are obtained (see Example 3).

Sources & evidence

ORD record
ord-8082984ff58e4c3c9047549ecb3a00b1
Source dataset
uspto-grants-1992_02
Patent number
US05091567

Reaction notes

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