4-Nitrobenzoic Acid → Methyl 2-(2-(4-nitrobenzoyl)-4,5-methylenedioxyphenyl)propionate

HRID 442676Notes

Reaction equation

HRID 442676 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=2[O:2]1.[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1)([O-:18])=[O:17].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C([O-])(O)=O.[Na+]>O.ClCCCl>[N+:16]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([C:6]2[CH:7]=[C:8]3[O:9][CH2:1][O:2][C:3]3=[CH:4][C:5]=2[CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[O:24])=[CH:26][CH:27]=1)([O-:18])=[O:17]

Participants

7

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 14812Phosphorus oxide (P4O10)HCID 516892Sodium BicarbonateHCID 453581932-Benzo[1,3]dioxol-5-YL-propanoic acid methyl ester

Product 1

HCID 53902600Methyl 2-(2-(4-nitrobenzoyl)-4,5-methylenedioxyphenyl)propionateYield 12.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a mixture of methyl 2-(3,4-methylenedioxyphenyl)propionate (1.0 g, 4.8 mmol), 4-nitrobenzoic acid (1.6 g, 9.6 mmol) and 1,2-dichloroethane (35 mL) was added P2O5 (4 g) and the mixture obtained was heated to reflux for 12 h. Water was added to the reaction mixture and it was neutralized to pH=7-8 by NaHCO3 solution. It was extracted with EtOAc and washed with brine. The product (211 mg, 12.3%) was obtained by a chromatographic purification (EtOAc:Hex=1:4). 1H NMR (CDCl3) 8.31 (d, J=8.7, 2H), 7.94 (d, J=8.7, 2H), 7.00 (s, 1H), 6.73 (s, 1H), 6.06 (s, 2H) 4.15 (q, J=7.1, 1H), 3.59 (s, 3H), 1.51 (d, J=7.1, 3H).

Workup

  1. customthe mixture obtained
  2. temperaturewas heated
  3. temperatureto reflux for 12 h
  4. extractionIt was extracted with EtOAc
  5. washwashed with brine

Sources & evidence

ORD record
ord-ad63b78daa7d408caea9767844a5d726
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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