2-Nitropropane → Methyl 4-formyl-2-methoxybenzoate

HRID 1906965Notes

Reaction equation

HRID 1906965 reaction equation
[N+](C(C)C)([O-])=[O:2].C[O-].[Na+].[C:10]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][C:15]=1[O:22][CH3:23])([O:12][CH3:13])=[O:11]>CO>[C:10]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:2])=[CH:16][C:15]=1[O:22][CH3:23])([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 10942334Sodium MethoxideHCID 11288398Methyl 4-(bromomethyl)-2-methoxybenzoate

Product 1

HCID 18510332Methyl 4-formyl-2-methoxybenzoateYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-Nitropropane (1.0 g) was added to sodium methoxide (from 0.24 g sodium) in methanol (30 ml) and the solution refluxed for 1/2 hour. 4-Carbomethoxy-3-methoxybenzyl bromide (2.67 g) in methanol was added and the solution refluxed for 1 hour. The methanol was evaporated, the residue partitioned between 2N sodium hydroxide and chloroform. The chloroform layer was shaken with further sodium hydroxide until no more yellow colour was extracted, dried and evaporated to yield the title compound (1.66 g). τ (CDCl3) 6.1 (3H, s), 6.05 (3H, s), 2.4-2.6 (2H, m), 2.07 (1H, d, J=8 Hz), -0.05 (1H, s).

Workup

  1. temperaturethe solution refluxed for 1/2 hour
  2. temperaturethe solution refluxed for 1 hour
  3. customThe methanol was evaporated
  4. customthe residue partitioned between 2N sodium hydroxide and chloroform
  5. extractionwas extracted
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-1aca89451d6e4f95afb7319e287fe12a
Source dataset
uspto-grants-1987_03
Patent number
US04654371

Reaction notes

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