Nitromethane → Methyl 3-(4-chlorophenyl)-4-nitrobutanoate

HRID 1380937Notes

Reaction equation

HRID 1380937 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl: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:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)[CH2:17][N+:14]([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 664601,1,3,3-TetramethylguanidineHCID 98955Methyl 3-(4-chlorophenyl)-2-propenoate

Product 1

HCID 14931333Methyl 3-(4-chlorophenyl)-4-nitrobutanoate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 290 g of p-chlorocinnamic acid methyl ester, 500 g of nitromethane and 39 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-(4-chlorophenyl)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-737fab49bd754684b3eda1ad3a03fefa
Source dataset
uspto-grants-1986_04
Patent number
US04584313

Reaction notes

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