Methanol → Methyl 5-tert-butyl-2-methoxy-3-nitro-benzoate

HRID 1844616Notes

Reaction equation

HRID 1844616 reaction equation
S(Cl)(Cl)=O.[C:5]([C:9]1[CH:10]=[C:11]([N+:20]([O-:22])=[O:21])[C:12]([O:18][CH3:19])=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15])([CH3:8])([CH3:7])[CH3:6].[CH3:23]O>>[C:5]([C:9]1[CH:10]=[C:11]([N+:20]([O-:22])=[O:21])[C:12]([O:18][CH3:19])=[C:13]([CH:17]=1)[C:14]([O:16][CH3:23])=[O:15])([CH3:8])([CH3:6])[CH3:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 508823195-(Tert-butyl)-2-methoxy-3-nitrobenzoic acid

Product 1

HCID 50882191Methyl 5-tert-butyl-2-methoxy-3-nitro-benzoate

Conditions

Temperature
60 °C

Procedure

2.3 ml of thionyl chloride are added dropwise to an ice-cooled solution of 5.40 g 5-tert-butyl-2-methoxy-3-nitro-benzoic acid in 50 ml of methanol. The cooling bath is removed and the solution is heated to 60° C. The solution is stirred overnight at 60° C. and then cooled to ambient temperature. The solution is evaporated down completely and the residue is mixed with water. The aqueous mixture is extracted with ethyl acetate, and the combined extracts are dried (MgSO4). The solvent is removed, and the residue is chromatographed on silica gel with cyclohexane/ethyl acetate (98:2→60:40).

Workup

  1. customThe cooling bath is removed
  2. temperaturecooled to ambient temperature
  3. customThe solution is evaporated down completely
  4. additionthe residue is mixed with water
  5. extractionThe aqueous mixture is extracted with ethyl acetate
  6. dry with materialthe combined extracts are dried (MgSO4)
  7. customThe solvent is removed
  8. customthe residue is chromatographed on silica gel with cyclohexane/ethyl acetate (98:2→60:40)

Sources & evidence

ORD record
ord-a35362493eee42148c5f60ea538f4b07
Source dataset
uspto-grants-2015_02
Patent number
US08946438B2

Reaction notes

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