Hydrogen Bromide → 4-benzyl-2-methylphenol

HRID 2254562Notes

Reaction equation

HRID 2254562 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([O:14]C)=[C:10]([CH3:16])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([CH3:16])[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 19742791HCID 19742791, compound

Product 1

HCID 2235054-benzyl-2-methylphenolYield 82.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 30.8 g of 4-benzyl-2-methyl-1-methoxybenzene with 50 ml of hydrobromic acid and 100 ml of acetic acid was refluxed with heating for 5 hours. This was left for cooling and neutralized with an aqueous sodium hydrogen-carbonate solution and was extracted twice with 100 ml of ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then was concentrated under reduced pressure. The resulting oily residue was chromatographed on a silica gel column (eluting solvent hexane : acetone=3 : 1 (v/v)) to obtain 23.7 g of 4-benzyl-2-methylphenol.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 5 hours
  3. waitThis was left
  4. temperaturefor cooling
  5. extractionwas extracted twice with 100 ml of ethyl acetate
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. concentrationwas concentrated under reduced pressure
  8. customThe resulting oily residue was chromatographed on a silica gel column (eluting solvent hexane : acetone=3 : 1 (v/v))

Sources & evidence

ORD record
ord-0ca374f6ddb0465ea45c16f1c3d3dc2c
Source dataset
uspto-grants-1993_08
Patent number
US05236924

Reaction notes

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