Methanol → HCID 11085581, compound

HRID 2401466Notes

Reaction equation

HRID 2401466 reaction equation
[Cl:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.[CH3:19]O>>[Cl:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:19])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 715128585-Chloro-2-methyl-4-nitrobenzoic acid

Product 1

HCID 11085581HCID 11085581, compoundYield 92%

Procedure

To 5-chloro-2-methyl-4-nitrobenzoic acid (900 mg, 4.15 mmol) in methanol (10 mL) was added thionyl chloride (0.3 mL, 4.15 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 5-chloro-2-methyl-4-nitrobenzoate (880 mg, 92%) as an off-white solid. LCMS (10 cm_ESCI_Formic_MeCN): [M+H]+=230 at 4.25 min. 1H NMR (400 MHz, CDCl3): δ 8.08 (s, 1H), 7.73 (s, 1H), 3.95 (s, 3H), 2.64 (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-8e30450ffcef4037942006c10c4100c3
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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