Hydrochloric Acid → (1-Nitromethylcyclohexyl)acetic acid ethyl ester

HRID 1535023Notes

Reaction equation

HRID 1535023 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1(=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[N+:19]([CH3:22])([O-:21])=[O:20].Cl>CS(C)=O.O>[N+:19]([CH2:22][C:7]1([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([O-:21])=[O:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 11430Potassium CarbonateHCID 73776Ethyl cyclohexylideneacetate

Product 1

HCID 11128083(1-Nitromethylcyclohexyl)acetic acid ethyl esterYield 88.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a mixture of 64.72 g (0.469 mole) potassium carbonate suspended in 469.5 mL dimethyl sulphoxide is measured in, during the course of 1 to 2 hours at 95° C., a solution of 158 g, (0.939 mole) ethyl cyclohexylideneacetate and 85.94 g (1.408 mole) nitromethane. After completion of the addition, stirring is continued at 95° C. for 2 to 3 hours. Subsequently, with ice-water cooling, the reaction solution is acidified with about 150 mL concentrated hydrochloric acid and diluted with 1.5 L of water. The resultant phases are separated and the aqueous phase is extracted several times with petroleum ether. The combined organic phases are washed neutral with water and dried over anhydrous sodium sulphate. The solvent is subsequently distilled off in a vacuum. 190.3 g Ethyl 1-nitromethyl-cyclohexaneacetate in the form of an oil are obtained; yield 88.4% of theory. Composition according to HPLC: 90% of the desired product of Step 2 and 6% ethyl cyclohexylideneacetate (Step 1).

Workup

  1. customduring the course of 1 to 2 hours
  2. customat 95° C.
  3. additionAfter completion of the addition
  4. customThe resultant phases are separated
  5. extractionthe aqueous phase is extracted several times with petroleum ether
  6. washThe combined organic phases are washed neutral with water
  7. dry with materialdried over anhydrous sodium sulphate
  8. distillationThe solvent is subsequently distilled off in a vacuum

Sources & evidence

ORD record
ord-27f300d0b40b444a9599d3f111d4e69c
Source dataset
uspto-grants-1992_02
Patent number
US05091567

Reaction notes

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