Sodium Hydroxide → 2,6-Difluoro-4-methylbenzoic acid

HRID 908243Notes

Reaction equation

HRID 908243 reaction equation
[OH-:1].[Na+].[F:3][C:4]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([F:13])[C:5]=1[CH:6]=[O:7]>[Ag]=O.O>[F:3][C:4]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([F:13])[C:5]=1[C:6]([OH:1])=[O:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 210638002,6-Difluoro-4-methylbenzaldehyde

Product 1

HCID 534034142,6-Difluoro-4-methylbenzoic acidYield 53%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 962WaterSolvent

Procedure

Silver oxide (43.8 g, 0.189 mol) was placed in a flask along with water (200 mL) and sodium hydroxide (33.7 g, 0.842 mol). To it was added 2,6-difluoro-4-methylbenzaldehyde (29.23 g, 0.187 mol) in small portions over a 30 min period. After a vigorous exothermic reaction, the color of the reaction mixture changed from black to gray. Resulting thick suspension was stirred for 1 hr, filtered through a Buchner funnel. The filtrate was acidified to pH 2 with concentrated HCl to give a suspension. The precipitate was collected by suction filtration, dissolved in ether and dried over anhydrous Na2SO4, filtered and concentrated to give white solid (17.0 g, 53%). 1H-NMR (500 MHz, d6-DMSO): δ13.7 (br.s, 1H), 7.02 (d, 2H, J=9.3 Hz), 2.32 (s, 3H).

Workup

  1. customAfter a vigorous exothermic reaction
  2. customResulting thick suspension
  3. filtrationfiltered through a Buchner funnel
  4. customto give a suspension
  5. filtrationThe precipitate was collected by suction filtration
  6. dissolutiondissolved in ether
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-dbc48b3241c94e8a9d11e311e4fd6b73
Source dataset
uspto-grants-2011_09
Patent number
US08017605B2

Reaction notes

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