Methane → 1-(2-Hydroxy-3-(trifluoromethyl)phenyl)ethan-1-one

HRID 1911276Notes

Reaction equation

HRID 1911276 reaction equation
[OH:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:15][Li].C>C1COCC1.CCOCC>[OH:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](=[O:6])[CH3:15]

Participants

6

Reactant 3

HCID 297MethaneHCID 108890392-Hydroxy-3-(trifluoromethyl)benzoic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 685942851-(2-Hydroxy-3-(trifluoromethyl)phenyl)ethan-1-oneYield 99%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

A solution of Example 42B (14.1 g, 68.4 mmol) in THF (70 mL) was cooled to 5° C. and methyllithium (133 mL of a 1.6M solution in Et2O, 212 mmol) was added, keeping the temperature≦20° C. (slow addition, methane generation). The cooling bath was removed and after 10 min, the reaction mixture was complete by LCMS. The reaction was cooled to 10° C. and EtOAc (140 mL) and 2N HCl (140 mL) were added. The layers were partitioned and the organic portion was washed with water (70 mL) and brine (28 mL). The organic portion was dried (Na2SO4), filtered, and concentrated, to give the title compound (14.0 g, 68.6 mmol, 99%) as an orange oil that was used without further purification. MS (DCI/NH3) m/z 222 (M+NH4)+.

Workup

  1. customThe cooling bath was removed and after 10 min
  2. additionEtOAc (140 mL) and 2N HCl (140 mL) were added
  3. customThe layers were partitioned
  4. washthe organic portion was washed with water (70 mL) and brine (28 mL)
  5. dry with materialThe organic portion was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fc14b2093ca44ecbb33c5050fc2c4eb0
Source dataset
uspto-grants-2013_12
Patent number
US08604053B2

Reaction notes

Loading…