2-Nitropropane → Methyl 2-(4-formylphenyl)benzoate

HRID 2254889

Reaction equation

HRID 2254889 reaction equation
[N+](C(C)C)([O-])=[O:2].Br[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1.[Na]>C(O)C>[CH:8]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1)=[O:2]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 5360545SodiumHCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylate

Product 1

HCID 4325150Methyl 2-(4-formylphenyl)benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Nitropropane (7.7 ml) and compound C (20.0 g) were added to a solution of sodium (1.52 ) in ethanol (80 ml) and the solution was heated under reflux for 5 hours. Volatile material was removed by evaporation and the residue was partitioned between ether (300 ml) and water (300 ml). The organic phase was separated, washed with saturated sodium chloride solution and dried (MgSO4). The solvent was removed by evaporation and the residue was purified by flash chromatography, eluting with a mixture of ethyl acetate and hexane (1:9 v/v gradually changing to 1:1 v/v), to give methyl 4'-formylbiphenyl-2-carboxylate (D) (10.2 g) as a waxy solid; NMR (d6 -DMSO): 3.6(s,3H), 7.45-7.6(m,4H), 7.7(d of t, 1H), 7.85(d of d, 1H), 7.95(d,2H), 10.05(s,1H).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 5 hours
  3. customVolatile material was removed by evaporation
  4. customthe residue was partitioned between ether (300 ml) and water (300 ml)
  5. customThe organic phase was separated
  6. washwashed with saturated sodium chloride solution
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed by evaporation
  9. customthe residue was purified by flash chromatography
  10. washeluting with a mixture of ethyl acetate and hexane (1:9 v/v

Sources & evidence

ORD record
ord-7e5edc54ac174d5ab50e5c8ae5652f28
Source dataset
uspto-grants-1993_08
Patent number
US05236937

Linked notes

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