Tetraethyl 2-(4-nitrophenyl)propane-1,1,3,3-tetracarboxylate → 3-(4-Nitrophenyl)pentanedioic acid

HRID 1008876Notes

Reaction equation

HRID 1008876 reaction equation
C([O:3][C:4](=[O:32])[CH:5](C(OCC)=O)[CH:6]([C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)[CH:7](C(OCC)=O)[C:8]([O:10]CC)=[O:9])C>Cl>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([CH:6]([CH2:7][C:8]([OH:10])=[O:9])[CH2:5][C:4]([OH:32])=[O:3])=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

3

Reactant 1

HCID 16744629Tetraethyl 2-(4-nitrophenyl)propane-1,1,3,3-tetracarboxylate

Product 1

HCID 184046303-(4-Nitrophenyl)pentanedioic acidYield 88%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 7.32 g (16.1 mmol) of 2,4-bis-ethoxycarbonyl-3-(4-nitro-phenyl)-pentanedioic acid diethyl ester (as prepared in the previous step) in concentrated HCl (15 mL) was heated to 100° C. for 22 h. The mixture was cooled to RT, and the resulting precipitate was filtered, washed with cold water, and air-dried to afford 3.58 g (88%) of the title compound as an off-white solid: 1H-NMR (CD3OD; 400 MHz): δ 8.12 (d, 2H, J=8.8 Hz), 7.58 (d, 2H, J=8.8 Hz), 3.77-3.68 (m, 1H), 2.87-2.66 (m, 4H).

Workup

  1. temperatureThe mixture was cooled to RT
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with cold water
  4. customair-dried

Sources & evidence

ORD record
ord-7ba57ce09f9841968614755a4f55e77c
Source dataset
uspto-grants-2011_07
Patent number
US07973035B2

Reaction notes

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