Hydrochloric Acid → 2'-Hydroxy-4'-methylacetophenone

HRID 1901124Notes

Reaction equation

HRID 1901124 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1)(=O)C.[Al+3].[Cl-].[Cl-].[Cl-].Cl.[CH3:17][CH2:18][O:19]CC>>[CH3:11][C:7]1[CH:8]=[CH:9][C:10]([C:18]([CH3:17])=[O:19])=[C:5]([OH:4])[CH:6]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67406CresatinHCID 6451240Aluminum(III) Chloride

Product 1

HCID 813382'-Hydroxy-4'-methylacetophenone

Conditions

Temperature
165 °C

Procedure

To 50 g (0.33 mol) of 3-acetoxytoluene from Step 1 was added AlCl3 (60 g, 0.45 mol) and the resulting mixture was heated at 165° C. for 20 min., then cooled to 0° C. and HCl 1N was carefully added followed by Et2O. The aqueous phase was extracted 5× with Et2O and the combined organic phase was washed with brine, dried over MgSO4 and evaporated. The residue was distilled under vacuum to give the title compound.

Workup

  1. temperaturecooled to 0° C.
  2. extractionThe aqueous phase was extracted 5× with Et2O
  3. washthe combined organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-228971a130f44330b67be3ea99b21c1a
Source dataset
uspto-grants-1996_11
Patent number
US05576338

Reaction notes

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