Nitromethane → Benzenepropanoic acid, b-(nitromethyl)-, methyl ester

HRID 1380929

Reaction equation

HRID 1380929 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N+:13]([CH3:16])([O-:15])=[O:14].CN(C)C(=N)N(C)C>C(OCC)C.Cl>[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH:5]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH2:16][N+:13]([O-:15])=[O:14]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 76442-Propenoic acid, 3-phenyl-, methyl esterHCID 664601,1,3,3-Tetramethylguanidine

Product 1

HCID 10537045Benzenepropanoic acid, b-(nitromethyl)-, methyl ester

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 300 g of cinnamic acid methyl ester, 500 g of nitromethane and 39 g of tetramethylguanidine is allowed to stir at room temperature for 72 hours. The solution is diluted with diethyl ether and aqueous hydrochloric acid solution (1 N, 1 liter) is added. The organic layer is separated, dried over anhydrous magnesium sulfate, and evaporated to give 4-nitro-3-phenylbutanoic acid methyl ester.

Workup

  1. additionis added
  2. customThe organic layer is separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-8047cb0e83d14c57a0028cc1464f6079
Source dataset
uspto-grants-1986_04
Patent number
US04584313

Linked notes

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