Methanol → Methyl 4-fluoro-2-methylbenzoate

HRID 2277623Notes

Reaction equation

HRID 2277623 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.O=S(Cl)Cl.[CH3:16]O>>[CH3:16][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=1[CH3:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 38606394-Fluoro-2-methylbenzoic acid

Product 1

HCID 2782181Methyl 4-fluoro-2-methylbenzoateYield 90.7%

Procedure

To a stirred solution of 4-fluoro-2-methyl-benzoic acid (13 g, 84 mmol) in MeOH (500 mL) was added SOCl2 (20 g, 168 mmol) dropwise at 0° C. After the addition, the reaction mixture was stirred at room temperature for 16 hours. When TLC indicated that no starting material was left, the mixture was concentrated under reduced pressure to give a crude product (12.7 g, yield 90.7%), which was used in the next step reaction without further purification.

Workup

  1. additionAfter the addition
  2. waitwas left
  3. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-76faf5ac50af4296bb6b660d3a8b9a8e
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

Loading…