Hydrochloric Acid → 1-(2-Fluoro-4-methylphenyl)-2-phenylethanone

HRID 1471925Notes

Reaction equation

HRID 1471925 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:22])[CH:10]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)C(OCC)=O.Cl.[OH-].[Na+]>C1COCC1.O>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:22])[CH2:10][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67384741Ethyl 3-(2-fluoro-4-methylphenyl)-3-oxo-2-phenylpropanoate

Product 1

HCID 673846201-(2-Fluoro-4-methylphenyl)-2-phenylethanoneYield 79.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-(2-fluoro-4-methylphenyl)-3-oxo-2-phenylpropanoate (8.0 g, 26.6 mmol) was dissolved in THF (20 mL) and hydrogen chloride (37% wt., 32.0 mL, 400 mmol) was added. The reaction was brought to reflux overnight. After cooled to room temperature, the reaction was diluted with H2O (100 mL) and neutralized to pH 8 with NaOH (4.0 M aq.). The mixture was extracted with EtOAc (3×75 mL), dried over MgSO4, and purified by column chromatography to give the title compound as a clear oil (4.81 g). LCMS m/z=229.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.36 (s, 3H), 4.28 (s, 2H), 7.11-7.18 (m, 2H), 7.19-7.26 (m, 3H), 7.27-7.34 (m, 2H), 7.77 (t, J=8.21 Hz, 1H).

Workup

  1. temperatureto reflux overnight
  2. extractionThe mixture was extracted with EtOAc (3×75 mL)
  3. dry with materialdried over MgSO4
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-04d69acf90754fd8bf3945a558a9658d
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

Loading…