Lithium Hydroxide → 3-(Difluoromethyl)benzoic acid

HRID 594027Notes

Reaction equation

HRID 594027 reaction equation
[F:1][CH:2]([F:13])[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8]C)=[O:7].[Li+].[OH-]>C1COCC1>[F:1][CH:2]([F:13])[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 66771812Benzoic acid, 3-(difluoromethyl)-, methyl ester

Product 1

HCID 144612963-(Difluoromethyl)benzoic acidYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(difluoromethyl)benzoate (1 equiv.) in THF (0.25M) was added 1M LiOH (2.5 equiv.) and allowed to stir at RT. Upon initial addition of LiOH, the solution turned from clear to a burnt orange, and after 2 hrs the solution is light yellow. The reaction stirred for 18 hrs at RT. The volatiles were removed in vacuo, and the aqueous phase was acidified to ˜pH 3. A white precipitate was formed, filtered and dried. Isolated 3-(difluoromethyl)benzoic acid in 78% yield. LCMS (m/z) (M+H)=245.1, Rt=0.73). 1H NMR (400 MHz, <dmso>) δ ppm 6.97-7.30 (m, 1H) 7.63-7.71 (m, 1H) 7.83 (d, J=7.43 Hz, 1H) 8.06-8.16 (m, 1H)

Workup

  1. customafter 2 hrs
  2. stirringThe reaction stirred for 18 hrs at RT
  3. customThe volatiles were removed in vacuo
  4. customA white precipitate was formed
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-a3e737d38ad54a3682095007195cf11e
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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