Methanol → HCID 71513518, compound

HRID 2401453Notes

Reaction equation

HRID 2401453 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:13]([O-:15])=[O:14])=[CH:5][C:6]([CH3:12])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9].S(Cl)(Cl)=O.[CH3:20]O>>[CH3:1][O:2][C:3]1[C:4]([N+:13]([O-:15])=[O:14])=[CH:5][C:6]([CH3:12])=[C:7]([CH:11]=1)[C:8]([O:10][CH3:20])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 201618455-Methoxy-2-methyl-4-nitrobenzoic acid

Product 1

HCID 71513518HCID 71513518, compoundYield 82%

Procedure

To 5-methoxy-2-methyl-4-nitrobenzoic acid (1.27 g, 6 mmol) in methanol (15 mL) was added thionyl chloride (0.44 mL, 6 mmol) dropwise. The mixture was heated to reflux for 3 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. Purification of the residue via silica gel column chromatography (0-100% EtOAc in iso-hexane) gave methyl 5-methoxy-2-methyl-4-nitrobenzoate (1.11 g, 82%) as an off-white solid. LCMS (10 cm_ESCI_Formic_MeCN): [M+H]+=226 at 3.92 min. 1H NMR (400 MHz, CDCl3): δ 7.68 (s, 1H), 7.60 (s, 1H), 3.98 (s, 3H), 3.95 (s, 3H), 2.55 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 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
  7. customPurification of the residue via silica gel column chromatography (0-100% EtOAc in iso-hexane)

Sources & evidence

ORD record
ord-70c217b3520b412c84ff711caa9ba5c1
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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