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

HRID 464729Notes

Reaction equation

HRID 464729 reaction equation
CO[C:3](=O)[CH:4]([N+:15]([O-:17])=[O:16])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)[CH3:6].[C:19]([O:23][CH3:24])(=[O:22])[CH:20]=C.Cl>C(O)(C)(C)C.C(OCC)C>[CH3:24][O:23][C:19](=[O:22])[CH2:6][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)[CH:4]([N+:15]([O-:17])=[O:16])[CH2:3][CH2:20][C:19]([O:23][CH3:24])=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 53981398Nitro-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 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-4a5723303e614c4e95d3aa2c520efabb
Source dataset
uspto-grants-1985_10
Patent number
US04548947

Reaction notes

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