Sulfuric Acid → HCID 178520888, compound

HRID 1242524Notes

Reaction equation

HRID 1242524 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.C([O:17][C:18](=O)[C:19]([F:22])([F:21])[F:20])C.OS(O)(=O)=O>C1(C)C=CC=CC=1>[F:20][C:19]([F:22])([F:21])/[C:18](/[OH:17])=[CH:11]/[C:10]([C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:13])([F:14])[F:1])=[CH:9][CH:8]=1)=[O:12]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 9794Ethyl trifluoroacetateHCID 5228211-(4-(Trifluoromethoxy)phenyl)ethan-1-one

Product 1

HCID 178520888HCID 178520888, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
2 °C

Procedure

25 g (122 mmol) 1-(4-Trifluoromethoxy-phenyl)-ethanone were added to a suspension of 16.5 g (147 mmol) potassium-tert-butylate in 250 ml toluene. The suspension was cooled to 2° C. and 17.5 ml (147 mmol) ethyltrifluoroacetate were added within 15 min. The mixture was stirred at ambient temperature for 14 h, cooled to 2° C. and brought to pH 6 with 10% aqueous H2SO4. Twofold extraction with tert-butyl methylether was followed by washing of the combined extracts with brine/ice water 1/1 and drying of the organic layer over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by flash chromatography (silica gel, dichloromethane) to give 30.5 g (102 mmol, 83%) of the title compound as red oil.

Workup

  1. temperaturecooled to 2° C.
  2. extractionTwofold extraction with tert-butyl methylether
  3. washby washing of the combined extracts with brine/ice water 1/1
  4. dry with materialdrying of the organic layer over sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue purified by flash chromatography (silica gel, dichloromethane)

Sources & evidence

ORD record
ord-405148a7a1e943418e94a9dbc85cefd0
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

Loading…