Methanol → Methyl 2-methyl-4-nitrobenzoate

HRID 1039085Notes

Reaction equation

HRID 1039085 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:19]O>>[CH3:6][C:7]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:8]=1[C:9]([O:11][CH3:19])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 747904-Nitro-o-toluic acid

Product 1

HCID 15088700Methyl 2-methyl-4-nitrobenzoate

Conditions

Temperature
55 °C

Procedure

Sulfuric acid (6 ml, 113 mmol) was added to drop wise to a solution of the 2-methyl-4-nitrobenzoic acid (5 g, 27.6 mmol) in MeOH (138 ml) at RT. After the addition was complete the mixture was heated to 55° C. overnight. The volatiles were removed in vacuum and the residue partitioned between EtOAc (100 ml) and water (100 ml). The layers were separated and aqueous phase extracted with EtOAc (2×100 ml). The organic fractions were combined, washed with saturated sodium bicarbonate (aqueous, 100 ml), brine, dried over Na2SO4, filtered and the volatiles removed in vacuum to give the titled compound.

Workup

  1. additionAfter the addition
  2. customThe volatiles were removed in vacuum
  3. customthe residue partitioned between EtOAc (100 ml) and water (100 ml)
  4. customThe layers were separated
  5. extractionaqueous phase extracted with EtOAc (2×100 ml)
  6. washwashed with saturated sodium bicarbonate (aqueous, 100 ml), brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customthe volatiles removed in vacuum

Sources & evidence

ORD record
ord-e45486ce10b94518a167680bb201e019
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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