Methanol → Methyl 4-(hydroxymethyl)-3-nitrobenzoate

HRID 2416207Notes

Reaction equation

HRID 2416207 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].[CH3:15]O>OS(O)(=O)=O>[CH3:15][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([CH2:2][OH:1])=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 15018924-Hydroxymethyl-3-nitrobenzoic acid

Product 1

HCID 10943774Methyl 4-(hydroxymethyl)-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
70 °C

Procedure

4-Hydroxymethyl-3-nitro-benzoic acid (step (a), 2.0 g, 10.2 mmol) was dissolved in 100 mL of MeOH, treated with 10 drops of concentrated H2SO4 and stirred at 70° C. After 36 h, the solution was concentrated in vacuo and redissolved in EtOAc. The EtOAc solution was washed with 1N NaOH and brine, dried over MgSO4, and concentrated to afford the title compound as a light-yellow solid upon drying under vacuum. MS m/z: 210.1 (M−1).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. dissolutionredissolved in EtOAc
  3. washThe EtOAc solution was washed with 1N NaOH and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-91887a49dcbf4a5ebbb0ffbfe966507f
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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