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

HRID 1380942Notes

Reaction equation

HRID 1380942 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH:5]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)[CH2:6][N+:7]([O-:9])=[O:8].[C:19]([O:23][CH3:24])(=[O:22])[CH:20]=[CH2:21].Cl>C(O)(C)(C)C.C(OCC)C>[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH:5]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)[CH:6]([N+:7]([O-:9])=[O:8])[CH2:21][CH2:20][C:19]([O:23][CH3:24])=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 214725024-Nitro-3-(3,4-dichlorophenyl)butanoic acid methyl ester

Product 1

HCID 537934914-Nitro-3-(3,4-dichlorophenyl)heptanedioic acid dimethyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 350 g of 4-nitro-3-(3,4-dichlorophenyl)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-(3,4-dichlorophenyl)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-7d098911b7184e22a70340d28e7a891b
Source dataset
uspto-grants-1986_04
Patent number
US04584313

Reaction notes

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