Hydrochloric Acid → 4-(2-Oxopropyl)benzoic acid

HRID 1633102Notes

Reaction equation

HRID 1633102 reaction equation
Cl.[C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]([N+]([O-])=O)[CH3:13])=[CH:7][CH:6]=1)([OH:4])=[O:3].[OH2:17]>O1CCOCC1.[Fe]>[CH2:11]([C:8]1[CH:9]=[CH:10][C:5]([C:2]([OH:4])=[O:3])=[CH:6][CH:7]=1)[C:12]([CH3:13])=[O:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 542582771-(4-Carboxyphenyl)-2-nitropropene

Product 1

HCID 5762444-(2-Oxopropyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 312751,4-DioxaneSolvent

Procedure

Concentrated hydrochloric acid (367 ml) was added dropwise to a mixture of 1-(4-carboxyphenyl)-2-nitroprop-1-ene (61.17 g) and iron powder (61.17 g) in dioxan (500 ml) at reflux. The heating was continued for 1 hour at the end of addition. The solution was cooled, water added, the dioxan evaporated and the residue extracted with chloroform and dried (MgSO4). Removal of the solvent gave a solid which was recrystallised from ethyl acetate to give 26 g of the title compound. τ (d6DMSO) 7.83 (3H, s), 6.14 (2H, s), 2.69 (2H, d, J=9 Hz), 2.05 (2H, d, J=9 Hz).

Workup

  1. temperatureat reflux
  2. additionThe heating was continued for 1 hour at the end of addition
  3. temperatureThe solution was cooled
  4. customthe dioxan evaporated
  5. extractionthe residue extracted with chloroform
  6. dry with materialdried (MgSO4)
  7. customRemoval of the solvent
  8. customgave a solid which
  9. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-bc39e9d84d004a36aee61b0fb43d99ab
Source dataset
uspto-grants-1984_10
Patent number
US04478849

Reaction notes

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