Hydrogen Bromide → HCID 20296986, compound

HRID 1389559Notes

Reaction equation

HRID 1389559 reaction equation
[CH:1]1([C:7]([C:9]2[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[CH:11][C:10]=2[O:19]C)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.I.Br>C(O)(=O)C>[CH:1]1([C:7]([C:9]2[CH:14]=[C:13]([C:15]([CH3:17])([CH3:16])[CH3:18])[CH:12]=[CH:11][C:10]=2[OH:19])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24841Hydrogen iodideHCID 20296956HCID 20296956, compound

Product 1

HCID 20296986HCID 20296986, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 1.70 g of 2-cyclohexylcarbonyl-4-tert-butylanisole [prepared in Reference Example 2 (a)] dissolved in 10 ml of glacial acetic acid were added 1.0 ml of 57% hydroiodic acid and 2.0 ml of 47% hydrobromic acid, and heated at reflux for 2 hours. The reaction mixture was poured into 50 ml of ice-water, extracted with diethyl ether, and the extract was washed with saturated aqueous sodium thiosulfate solution, 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 1.54 g of the title compound having the following physical properties.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. extractionextracted with diethyl ether
  4. washthe extract was washed with saturated aqueous sodium thiosulfate solution, water and saturated brine successively
  5. dry with materialdried over magnesium sulfate anhydride
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was chromatographed on silica gel column

Sources & evidence

ORD record
ord-d7734c5f67cc43ae84cfe51b6aa5a2f3
Source dataset
uspto-grants-1981_01
Patent number
US04245099

Reaction notes

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