Hydrogen Bromide → 4-Hydroxyphenylacetone

HRID 479877Notes

Reaction equation

HRID 479877 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10](=[O:12])[CH3:11])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 312311-(p-Methoxyphenyl)-2-propanone

Product 1

HCID 70192744-Hydroxyphenylacetone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 82 g of 1-(4-methoxyphenyl)-2-propanone, 500 ml of acetic acid and 500 ml of aqueous hydrobromic acid is boiled under reflux for 2 hours and then evaporated in vacuo. The oily residue is extracted four times with 700 ml of hexane/ether (5:2) each time, the extract is evaporated and the residue is chromatographed over silica gel using hexanelethyl acetate (3:1). 1-(4-Hydroxyphenyl)-2-propanone is thus obtained with a melting point of 40-41°.

Workup

  1. temperatureunder reflux for 2 hours
  2. customevaporated in vacuo
  3. extractionThe oily residue is extracted four times with 700 ml of hexane/ether (5:2) each time
  4. customthe extract is evaporated
  5. customthe residue is chromatographed over silica gel using hexanelethyl acetate (3:1)

Sources & evidence

ORD record
ord-1e2ebca13380423ebbbb50fe640332c8
Source dataset
uspto-grants-2003_11
Patent number
US06646151B1

Reaction notes

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