Methanol → Benzoic acid, 3-fluoro-, methyl ester

HRID 128479

Reaction equation

HRID 128479 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[CH3:11][OH:12]>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:12][CH3:11])=[O:6]

Participants

3

Reactant 2

HCID 887MethanolHCID 743763-Fluorobenzoyl chloride

Product 1

HCID 521184Benzoic acid, 3-fluoro-, methyl esterYield 92.5%

Procedure

To a 1-liter flask fitted with a stirrer, addition funnel, condenser, and drying tube containing diethyl ether (200 ml) and methanol (anhd.; 64 g,; 2.0 moles] is added dropwise m-fluorobenzoyl chloride (317 g,; 2.0 moles) at room temperature over a 3 hour period. Additional methanol (10 ml) is added and the reaction mixture is stirred at room temperature overnight. The reaction mixture is then filtered through a bed of silicic acid and the solvent removed under vacuum to afford 285 grams of methyl 3-fluorobenzoate (92.5% yield). This was identical to the product prepared in Example 2A.

Workup

  1. customTo a 1-liter flask fitted with a stirrer, addition funnel, condenser
  2. customdrying tube
  3. additioncontaining diethyl ether (200 ml) and methanol (anhd
  4. filtrationThe reaction mixture is then filtered through a bed of silicic acid
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-0cc6afdb11fa47bbab9a7eb35c8c2e80
Source dataset
uspto-grants-1981_03
Patent number
US04259510

Linked notes

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