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

HRID 464728Notes

Reaction equation

HRID 464728 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1.[N+:15]([CH3:18])([O-:17])=[O:16].CN(C)C(=N)N(C)C>C(OCC)C.Cl>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH:5]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)[CH2:18][N+:15]([O-:17])=[O:16]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 664601,1,3,3-TetramethylguanidineHCID 54151376Methyl 3-(3,4-dichlorophenyl)prop-2-enoate

Product 1

HCID 214725024-Nitro-3-(3,4-dichlorophenyl)butanoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 300 g of 3,4-dichlorocinnamic acid methyl ester, 400 g of nitromethane and 26 g of tetramethylguanidine is allowed to stir for 72 hours. The solution is diluted with ethyl 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-(3,4-dichlorophenyl)butanoic 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-a5462e0316cc4d8eaf0de03e347fea08
Source dataset
uspto-grants-1985_10
Patent number
US04548947

Reaction notes

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