Methanol → 4-(1,3-Dioxolan-2-yl)-2-fluorobenzoic acid

HRID 736700Notes

Reaction equation

HRID 736700 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[C:8]([F:16])[CH:7]=1.O.[OH-].[Li+].CO>O1CCCC1.O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[C:8]([F:16])[CH:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 67353522Methyl 4-(1,3-dioxolan-2-yl)-2-fluorobenzoate

Product 1

HCID 673539164-(1,3-Dioxolan-2-yl)-2-fluorobenzoic acidYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 20C (2.0 g) in tetrahydrofuran (10 mL) and water (5 mL) was added lithium hydroxide monohydrate (1 g) in water (5 mL). Methanol was added until a transparent solution formed and the solution stirred at ambient temperature for 4 hours and concentrated to about 5 mL. The residue was acidified with 2N HCl to pH 2 and the mixture partitioned between ethyl acetate and water. The organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated to give the title compound (1.5 g, 79%). MS (DCI): m/z 213 (M+H)+.

Workup

  1. customformed
  2. concentrationconcentrated to about 5 mL
  3. customthe mixture partitioned between ethyl acetate and water
  4. washThe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ba49d857ac814f6e80393487c31fe7d1
Source dataset
uspto-grants-2009_09
Patent number
US07595406B2

Reaction notes

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