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

HRID 1673148Notes

Reaction equation

HRID 1673148 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 17C (2.0 g) in tetrahydrofuran (10 mL) and water (5 mL) was added a solution of lithium hydroxide monohydrate (1 g) in water (5 mL). Methanol was added until a homogeneous solution formed. The solution was stirred at ambient temperature for 4 hours and concentrated to 5 mL. This was acidified with 2N hydrochloric acid to pH 2 and partitioned between ethyl acetate and water. The organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated to give 1.5 g (79%) of the title compound. MS (DCI): m/z 213 (M+H)+.

Workup

  1. customformed
  2. concentrationconcentrated to 5 mL
  3. custompartitioned 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-2f1717894ac94bb4977506e6b966023c
Source dataset
uspto-grants-2011_08
Patent number
US07999117B2

Reaction notes

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