Methanol → Methyl (3-fluoro-4-methylphenyl)acetate

HRID 968968Notes

Reaction equation

HRID 968968 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].S(=O)(=O)(O)O.[CH3:18]O>>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:18])=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27746183-Fluoro-4-methylphenylacetic acid

Product 1

HCID 59016695Methyl (3-fluoro-4-methylphenyl)acetate

Conditions

Temperature
85 °C

Procedure

(3-Fluoro-4-methylphenyl)acetic acid (105.3 g) was dissolved in methanol (740 ml) and concentrated sulfuric acid (9.9 ml) was added. The mixture was stirred at 85° C. for 1 hr. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. Water was added to the obtained residue and the mixture was extracted with ethyl acetate (1 L). The organic layer was washed successively with water, aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (114.2 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionWater was added to the obtained residue
  4. extractionthe mixture was extracted with ethyl acetate (1 L)
  5. washThe organic layer was washed successively with water, aqueous sodium hydrogencarbonate solution, water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55ff220c72f946da93332ae138e336a0
Source dataset
uspto-grants-2007_12
Patent number
US07304174B2

Reaction notes

Loading…