Methanol → HCID 86687920, compound

HRID 2401459Notes

Reaction equation

HRID 2401459 reaction equation
[CH3:1][O:2][C:3]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:15])[CH:4]=1.S(Cl)(Cl)=O.[CH3:20]O>>[CH3:1][O:2][C:3]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:6]([C:7]([O:9][CH3:20])=[O:8])=[C:5]([CH3:15])[CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 86687919HCID 86687919, compound

Product 1

HCID 86687920HCID 86687920, compoundYield 89%

Procedure

To 4-methoxy-2-methyl-5-nitrobenzoic acid (1.06 g, 5 mmol) in methanol (10 mL) was added thionyl chloride (0.36 mL, 5 mmol) dropwise. The mixture was heated to reflux for 5 h and then allowed to cool. The solvent was removed in vacuo and the residue was partitioned between DCM (20 mL) and saturated aqueous NaHCO3 (20 mL). The organic phase was passed through a hydrophobic frit and the solvent was removed in vacuo to give methyl 4-methoxy-2-methyl-5-nitrobenzoate (998 mg, 89%) as an off-white solid. LCMS (10 cm_ESCI_Bicarb_MeCN): [M+H]+=226 at 3.25 min. 1H NMR (400 MHz, CDCl3): δ 8.56 (s, 1H), 6.91 (s, 1H), 4.01 (s, 3H), 3.90 (s, 3H), 2.71 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 h
  3. temperatureto cool
  4. customThe solvent was removed in vacuo
  5. customthe residue was partitioned between DCM (20 mL) and saturated aqueous NaHCO3 (20 mL)
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-bf16da4f21ae4e11b3084e8f0e9ae5bc
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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