Hydrochloric Acid → 1-(5-Bromo-2-hydroxyphenyl)propan-1-one

HRID 1416175Notes

Reaction equation

HRID 1416175 reaction equation
C([O:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)(=O)CC.[Cl-].[Al+3].[Cl-].[Cl-].Cl>>[Br:12][C:9]1[CH:10]=[CH:11][C:6]([OH:5])=[C:7]([C:6](=[O:5])[CH2:7][CH3:8])[CH:8]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 90205p-Bromophenyl propionateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 7364091-(5-Bromo-2-hydroxyphenyl)propan-1-oneYield 191.3%

Procedure

4-Bromophenyl propionate (115 g) (see Preparation 1) and aluminium chloride (150 g) were heated together at approximately 90° C. for 15 minutes. The solution became dark and hydrogen chloride gas was evolved. After cooling the black mass was carefully added to ice and a brown solid formed. The mixture was extracted with dichloromethane. The organic extract was separated, washed with brine, dried (anhydrous magnesium sulphate) and the solvent removed under reduced pressure to yield 1-(5-bromo-2-hydroxyphenyl)propan-1-one (110 g) as a yellow solid.

Workup

  1. temperatureAfter cooling the black mass
  2. additionwas carefully added to ice
  3. customa brown solid formed
  4. extractionThe mixture was extracted with dichloromethane
  5. extractionThe organic extract
  6. customwas separated
  7. washwashed with brine
  8. dry with materialdried (anhydrous magnesium sulphate)
  9. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c479031725ce44fd971084f50ff4647f
Source dataset
uspto-grants-1999_06
Patent number
US05912244

Reaction notes

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