Nitromethane → 4-Nitro-3-(4-trifluoromethylphenyl)butanoic acid ethyl ester

HRID 1380945Notes

Reaction equation

HRID 1380945 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)[CH3:2].[N+:18]([CH3:21])([O-:20])=[O:19].CN(C)C(=N)N(C)C>C(OCC)C.Cl>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH:6]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:15])([F:16])[F:14])=[CH:9][CH:8]=1)[CH2:21][N+:18]([O-:20])=[O:19])[CH3:2]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 664601,1,3,3-TetramethylguanidineHCID 53662772Ethyl 3-[4-(trifluoromethyl)phenyl]prop-2-enoate

Product 1

HCID 539494754-Nitro-3-(4-trifluoromethylphenyl)butanoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 300 g of 4-trifluoromethylcinnamic acid ethyl ester, 500 g of nitromethane, and 39 g of tetramethylguanidine is allowed to stir 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-(4-trifluoromethylphenyl)butanoic acid ethyl 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-7f33787321e34a98b134556a64b4d24b
Source dataset
uspto-grants-1986_04
Patent number
US04584313

Reaction notes

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