Methanol → Methyl 4-fluoro-2-methylbenzoate

HRID 1803865Notes

Reaction equation

HRID 1803865 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.[CH3:12]O>OS(O)(=O)=O>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[C:4]([CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 38606394-Fluoro-2-methylbenzoic acid

Product 1

HCID 2782181Methyl 4-fluoro-2-methylbenzoateYield 78%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

In a cylindrical quartz tube was placed 4-fluoro-2-methyl-benzoic acid (1.5 g, 9.7 mmol) in MeOH (15 ml) and 2 drops of H2SO4 conc. were added. The tube was introduced into a Smith Creator® Personal chemistry microwave reactor. Microwave irradiation was carried out at 130° C. for 1 h until HPLC revealed the disappearance of the starting-material. The mixture was allowed to cool down and the solvent was removed under reduced pressure. The crude was diluted with DCM and washed with NaHCO3 sat. The organic phase was dried over anhydrous Na2SO4 and concentration of the solution gave the final compound (1.3 g, 78%) as colourless oil.

Workup

  1. customIn a cylindrical quartz tube was placed
  2. additionThe tube was introduced into a Smith Creator® Personal chemistry microwave reactor
  3. customMicrowave irradiation
  4. temperatureto cool down
  5. customthe solvent was removed under reduced pressure
  6. additionThe crude was diluted with DCM
  7. washwashed with NaHCO3 sat. The organic phase
  8. dry with materialwas dried over anhydrous Na2SO4 and concentration of the solution

Sources & evidence

ORD record
ord-0b41183c7aad419397fc7c4d4b59ff4d
Source dataset
uspto-grants-2013_01
Patent number
US08354399B2

Reaction notes

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