Potassium Hydroxide → 4-(1,1,1-Trifluoro-2-hydroxypropan-2-yl)benzoic acid

HRID 1821156Notes

Reaction equation

HRID 1821156 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1)([OH:5])[CH3:4].[OH-].[K+]>O1CCOCC1.O>[F:1][C:2]([F:16])([F:17])[C:3]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)([OH:5])[CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 57892524Methyl 4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)benzoate

Product 1

HCID 578925274-(1,1,1-Trifluoro-2-hydroxypropan-2-yl)benzoic acidYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)benzoate (6.0 g, 24.2 mmol) and KOH (2.72 g, 48.4 mmol) in 1,4-dioxane (100 mL) and H2O (50 mL) was refluxed for 2 h. The reaction mixture was cooled to room temperature, and 1,4-dioxane evaporated in vacuo. The aqueous residue was acidified with 2N HCl and extracted with CH2Cl2. The extracts were washed with brine and dried. Flash chromatography of the residue, using 3:7 EtOAc-Hexane, gave 4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)benzoic acid (4.93 g). 1H NMR (CDCl3) δ 11.0(br, 1 H), 7.95(d, J=6.8 Hz, 2 H), 7.71(d, J=6.8 Hz, 2 H), 6.73 (s, 1 H), 1.71(s, 3H). MS 235.0 (M+H+).

Workup

  1. temperaturewas refluxed for 2 h
  2. custom1,4-dioxane evaporated in vacuo
  3. extractionextracted with CH2Cl2
  4. washThe extracts were washed with brine
  5. customdried

Sources & evidence

ORD record
ord-cfa7289b257c443d939ad35c012e3eac
Source dataset
uspto-grants-2009_10
Patent number
US07605289B2

Reaction notes

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