Hydrogen Bromide → HCID 15125079, compound

HRID 373370Notes

Reaction equation

HRID 373370 reaction equation
[CH2:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([O:10]C)=[C:5]([CH3:12])[C:4]=1[CH3:13])[CH3:2].Br>O>[CH2:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([OH:10])=[C:5]([CH3:12])[C:4]=1[CH3:13])[CH3:2]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 15125069HCID 15125069, compound

Product 1

HCID 15125079HCID 15125079, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4-ethyl-2,3,5-trimethylanisole (7.8 g) was added 47% aqueous hydrogen bromide solution and the mixture was refluxed for 17 hours. Water was added to the solution and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate, water and saturated saline and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was recrystallized from hexane to obtain 4-ethyl-2,3,5-trimethylphenol (3.6 g) (Compound A-17). The physical properties and NMR spectrum data thereof are shown in Table 1.

Workup

  1. temperaturethe mixture was refluxed for 17 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with aqueous sodium hydrogen carbonate, water and saturated saline
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-df4ef584a12f44048f18435f2f2be4b3
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

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