Hydrochloric Acid → 4-Nitro-3-(4-chlorophenyl)heptanedioic acid dimethyl ester

HRID 1380938Notes

Reaction equation

HRID 1380938 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH:5]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[CH2:6][N+:7]([O-:9])=[O:8].[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20].Cl>C(O)(C)(C)C.C(OCC)C>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH:5]([C:10]1[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=1)[CH:6]([N+:7]([O-:9])=[O:8])[CH2:20][CH2:19][C:18]([O:22][CH3:23])=[O:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 14931333Methyl 3-(4-chlorophenyl)-4-nitrobutanoate

Product 1

HCID 540468684-Nitro-3-(4-chlorophenyl)heptanedioic acid dimethyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 337 g of 4-nitro-3-(4-chlorophenyl)butanoic acid methyl ester, 118 g of methyl acrylate, and 25 ml of Triton B in 500 ml of t-butanol is allowed to stir at room temperature for 94 hours. Excess aqueous hydrochloric acid (1 N) is added and the solution is diluted with diethyl ether. The organic layer is separated, dried over anhydrous magnesium sulfate and evaporated to give 4-nitro-3-(4-chlorophenyl)heptanedioic acid dimethyl ester.

Workup

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

Sources & evidence

ORD record
ord-e20d3e507e144d9fb62ba9f1fd33b39a
Source dataset
uspto-grants-1986_04
Patent number
US04584313

Reaction notes

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