Methyl Acrylate → Rac-4-cyclohexyl-4-nitro-butyric acid methyl ester

HRID 2177486

Reaction equation

HRID 2177486 reaction equation
[N+:1]([CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)([O-:3])=[O:2].[C:11]([O:15][CH3:16])(=[O:14])[CH:12]=[CH2:13]>C(O)(C)(C)C.[OH-].C([N+](C)(C)C)C1C=CC=CC=1.CO.O>[CH3:16][O:15][C:11](=[O:14])[CH2:12][CH2:13][CH:4]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[N+:1]([O-:3])=[O:2]

Participants

7

Reactant 2

HCID 7294Methyl AcrylateHCID 220634(Nitromethyl)cyclohexane

Product 1

HCID 59438496Rac-4-cyclohexyl-4-nitro-butyric acid methyl ester

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 66854Benzyltrimethylammonium hydroxideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 3.18 g (22.2 mmol) nitromethyl-cyclohexane (CAS: 2625-30-1) in 1 ml tert-butanol and 0.12 ml 35% benzyltrimethylammonium hydroxide in methanol warmed to 40° C. were added 1.99 ml (22.2 mmol) methyl acrylate. The yellow mixture was stirred at 40° C. for 2 hours then diluted with water and extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, filtered and evaporated. The title compound was obtained in as slightly yellow oil: MS (EI): 198 (M.+−MeO), 183 (M.+−NO2), 151 (M−(MeO+NO2+H)).+ (100%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-96e1426b49f64e8294b979625162717f
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Linked notes

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