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

HRID 741824

Reaction equation

HRID 741824 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 at 0° C. and HCl 1N was carefully added followed by Et2O. The aqueous phase was extracted 5× with ET2O and the combined organic phase wash washed with brine, dried over MgSO4 and evaporated. The residue was distilled under vacuum to give 42.2 (84%) of the title compound.

Workup

  1. temperaturecooled at 0° C.
  2. extractionThe aqueous phase was extracted 5× with ET2O
  3. washthe combined organic phase wash
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-08260e7c4ff442b39621bd32023313c1
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Linked notes

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