Nitromethane → 4-Nitro-3-(4-methylphenyl) butanoic acid methyl ester

HRID 1380933Notes

Reaction equation

HRID 1380933 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1.[N+:14]([CH3:17])([O-:16])=[O:15].CN(C)C(=N)N(C)C>C(OCC)C.Cl>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH:5]([C:6]1[CH:7]=[CH:8][C:9]([CH3:12])=[CH:10][CH:11]=1)[CH2:17][N+:14]([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 664601,1,3,3-TetramethylguanidineHCID 589472Methyl 3-(4-methylphenyl)-2-propenoate

Product 1

HCID 540828904-Nitro-3-(4-methylphenyl) butanoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture to 300 g of p-methylcinnamic 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 (1 liter, 1 N) aqueous hydrochloric acid solution added. The organic layer is separated, dried over anhydrous magnesium sulfate, and evaporated to give 4-nitro-3-(4-methylphenyl) butanoic acid methyl ester.

Workup

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

Sources & evidence

ORD record
ord-fa303996e9374b23a7f92857c9d2d950
Source dataset
uspto-grants-1986_04
Patent number
US04584313

Reaction notes

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