Sulfuric Acid → 2-Trifluoroacetyl-4-tert-butylanisole

HRID 1389561Notes

Reaction equation

HRID 1389561 reaction equation
[Mg].I[C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:6]=[CH:5][C:4]=1[O:13][CH3:14].[F:15][C:16]([F:21])([F:20])[C:17](O)=[O:18].S(=O)(=O)(O)O>C(OCC)C>[F:15][C:16]([F:21])([F:20])[C:17]([C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:6]=[CH:5][C:4]=1[O:13][CH3:14])=[O:18]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 5462224MagnesiumHCID 149144624-Tert-butyl-2-iodo-1-methoxybenzene

Product 1

HCID 202969942-Trifluoroacetyl-4-tert-butylanisole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To 0.73 g of magnesium suspended in 5 ml of diethyl ether were added dropwise, under nitrogen, 8.70 g of 2-iodo-4-tert-butylanisole [described in Reference Example 1(a)] dissolved in 15 ml of diethyl ether and heated at reflux for one hour. To this solution were added dropwise 0.74 ml of trifluoroacetic acid dissolved in 3 ml of diethyl ether at room temperature, and heated at reflux for 1.5 hours. The reaction mixture was poured into ice-water, acidified with conc. sulfuric acid and extracted with diethyl ether. The extract was washed with water and saturated brine successively, dried over magnesium sulfate anhydride and concentrated at reduced pressure. The residue was chromatographed on silica gel column using a mixed solvent of methylene chloride and cyclohexane (1:2) as an eluting agent to give 1.83 g of the title compound having the following physical properties as pale yellow oil.

Workup

  1. additionwere added dropwise, under nitrogen
  2. temperatureheated
  3. temperatureat reflux for one hour
  4. temperatureheated
  5. temperatureat reflux for 1.5 hours
  6. extractionextracted with diethyl ether
  7. washThe extract was washed with water and saturated brine successively
  8. dry with materialdried over magnesium sulfate anhydride
  9. concentrationconcentrated at reduced pressure
  10. customThe residue was chromatographed on silica gel column

Sources & evidence

ORD record
ord-5e76ed1f017943c980ad6ef44f192297
Source dataset
uspto-grants-1981_01
Patent number
US04245099

Reaction notes

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