Lithium hydroxide, monohydrate → 4-(5-(Trifluoromethyl)isoxazol-3-yl)benzoic acid

HRID 1514083Notes

Reaction equation

HRID 1514083 reaction equation
C([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=2)=[CH:7][CH:6]=1)C.O.[OH-].[Li+]>C1COCC1>[F:19][C:16]([F:17])([F:18])[C:14]1[O:13][N:12]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:20])=[O:3])=[CH:6][CH:7]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 576061044-(5-Trifluoromethyl-isoxazol-3-yl)-benzoic acid ethyl ester

Product 1

HCID 576061124-(5-(Trifluoromethyl)isoxazol-3-yl)benzoic acidYield 73.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(5-Trifluoromethyl-isoxazol-3-yl)-benzoic acid ethyl ester (Preparative Example 9, 2.25 g, 7.86 mmol) in THF (20 mL) was treated with an aqueous solution (5 mL) of lithium hydroxide monohydrate (660 mg, 15.72 mmol) and allowed to stir for 16 hr. The reaction was then evaporated to a small volume and treated with a 1 N aqueous hydrochloric acid solution (25 mL) and the resulting solids filtered, washed with water and air dried to afford product as a colorless solid (1.48 g, 73%). 1H NMR (DMSO-d6) 8.06 (s, 4 H), 8.13 (s, 1 H). 13C NMR 106.5, 118.0 (q, J=270), 127.9, 130.8, 131.2, 132.4, ˜150 quartet not resolved from baseline noise, 133.8, 162.8, 167.3. 19F NMR −63.6. LC/MS 6.04 min, [M+1]+ 258.

Workup

  1. customThe reaction was then evaporated to a small volume
  2. additiontreated with a 1 N aqueous hydrochloric acid solution (25 mL)
  3. filtrationthe resulting solids filtered
  4. washwashed with water and air
  5. customdried

Sources & evidence

ORD record
ord-08442ceb9c7d47bc96eb5112a5018cac
Source dataset
uspto-grants-2012_07
Patent number
US08222243B2

Reaction notes

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