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

HRID 2360504Notes

Reaction equation

HRID 2360504 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:16]([O-:18])=[O:17])[C:8]([O:14][CH3:15])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.O.[C:24](OCC)(=O)C>CO>[C:1]([C:5]1[CH:6]=[C:7]([N+:16]([O-:18])=[O:17])[C:8]([O:14][CH3:15])=[C:9]([CH:13]=1)[C:10]([O:12][CH3:24])=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 508823195-(Tert-butyl)-2-methoxy-3-nitrobenzoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

5.4 g 5-tert-butyl-2-methoxy-3-nitro-benzoic acid are dissolved in 50 ml of methanol, cooled to 0° C. and combined dropwise with 2.32 ml of thionyl chloride. After the addition has ended the mixture is heated for 12 hours to 60° C. Then the solvents are eliminated in vacuo, the residue is divided between water and ethyl acetate and the aqueous phase is extracted twice with ethyl acetate. The combined organic phases are dried on magnesium sulphate and the solvent is eliminated in vacuo. The residue thus obtained is chromatographed on silica gel (cyclohexane/ethyl acetate (98:2 to 60:40).

Workup

  1. additionAfter the addition
  2. temperatureis heated for 12 hours to 60° C
  3. extractionthe aqueous phase is extracted twice with ethyl acetate
  4. customThe combined organic phases are dried on magnesium sulphate
  5. customThe residue thus obtained
  6. customis chromatographed on silica gel (cyclohexane/ethyl acetate (98:2 to 60:40)

Sources & evidence

ORD record
ord-44acfbbeb336467bbe52546cca3a727b
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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