Acetone → Methyl 3-fluoro-2-methoxybenzoate

HRID 330386Notes

Reaction equation

HRID 330386 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5](O)=[O:6])[C:3]=1O.IC.[C:14](=[O:17])([O-])[O-].[K+].[K+].[CH3:20]C(C)=O.[OH2:24]>>[F:1][C:2]1[C:3]([O:17][CH3:14])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:6][CH3:20])=[O:24]

Participants

6

Reactant 5

HCID 180AcetoneHCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2687243-Fluoro-2-hydroxybenzoic acid

Product 1

HCID 19862628Methyl 3-fluoro-2-methoxybenzoate

Procedure

A mixture containing 3-fluorosalicylic acid (20 g) [obtained as white crystals, m.p. 145°-147° C., by the method of L. N. Ferguson et alia, J. Amer. Chem. Soc., 1950, 72, 5315], iodomethane (60 g), potassium carbonate (40 g) and acetone (200 ml) was heated under reflux for 24 hours. Water (500 ml) was added and the mixture was extracted with ether (3×150 ml). The combined extracts were dried (MgSO4) and evaporated to give methyl 3-fluoro-2-methoxybenzoate (B) (21 g) as a yellow oil, which was used without further purification; NMR: 3.85 (3H,s), 3.95 (3H,s) and 6.8-7.6 (3H,m).

Workup

  1. customobtained as white crystals, m.p. 145°-147° C., by the method of L
  2. temperatureunder reflux for 24 hours
  3. extractionthe mixture was extracted with ether (3×150 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-e72ea964be6a412085cce6974b090cbf
Source dataset
uspto-grants-1990_01
Patent number
US04895962

Reaction notes

Loading…