Hydrogen Bromide → 1-Bromocyclohexyl 3,5-dimethyl-2-methoxyphenyl ketone

HRID 2051407Notes

Reaction equation

HRID 2051407 reaction equation
[CH3:1][C:2]1[C:3]([O:17][CH3:18])=[C:4]([C:9]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[BrH:19].BrBr>C(O)(=O)C>[CH3:1][C:2]1[C:3]([O:17][CH3:18])=[C:4]([C:9]([C:11]2([Br:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 15157169Cyclohexyl 3,5-dimethyl-2-methoxyphenyl ketone

Product 1

HCID 151571721-Bromocyclohexyl 3,5-dimethyl-2-methoxyphenyl ketone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

285.2 Grams of cyclohexyl 3,5-dimethyl-2methoxyphenyl ketone was dissolved in 800 ml of acetic acid. To the solution was added 8 ml of 47% hydrobromic acid and then a solution prepared by dissolving 212 g of bromine in 100 ml of acetic acid was added thereto dropwise with ice-cooling and stirring. After stirring at room temperature for 2 hours, the reaction mixture was poured into ice water, followed by extraction with 2 liters of ethyl acetate. The extract was washed with water and then with a saturated aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to obtain 363.6 g of 1-bromocyclohexyl 3,5-dimethyl-2-methoxyphenyl ketone.

Workup

  1. customa solution prepared
  2. additionwas added
  3. temperaturedropwise with ice-cooling
  4. stirringAfter stirring at room temperature for 2 hours
  5. extractionfollowed by extraction with 2 liters of ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialwith a saturated aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-58a8150a4e304f058f0e9d13d38352c8
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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