Hydrochloric Acid → {3-Cyano-6-[(4-fluorophenyl)carbonyl]phenyl}methyl 2,2-dimethylpropanoate

HRID 2187126Notes

Reaction equation

HRID 2187126 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[OH:18])=[C:7]([CH:16]=1)[CH2:8][O:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])#[N:2].OO.Cl>C(OC(=O)C)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[O:18])=[C:7]([CH:16]=1)[CH2:8][O:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 11256325HCID 11256325, compound

Product 1

HCID 11302208{3-Cyano-6-[(4-fluorophenyl)carbonyl]phenyl}methyl 2,2-dimethylpropanoateYield 97.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2,2-dimethyl-propionic acid 5-cyano-2-[1-(4fluoro-phenyl)-1-hydroxy-methyl]-benzyl ester (8.0 g, 0.025 mol) in ethylacetate (20 mL) was added hydrogen peroxide solution 30% wt (10 g, 0.079 mol), Na2WO4.2H2O (0.15 g, 0.0005 mol), and (n-Octyl)3NCH3.HSO4 (0.23 g, 0.0005 mol). The mixture was then heated at reflux for 4 hrs, allowed to cool to room temperature and pored into dilute HCl, extracted with diethyl ether (2×50 mL), dried (MgSO4) and concentrated under reduced pressure to give the title ketone compound (7.8 g, 97.5%).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 4 hrs
  3. extractionextracted with diethyl ether (2×50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2010169f5e934cc3b6e5a925467bae90
Source dataset
uspto-grants-2002_06
Patent number
US06407267B1

Reaction notes

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