Acetyl chloride → 1-(5-Tert-butyl-2-hydroxyphenyl)ethan-1-one

HRID 1389558Notes

Reaction equation

HRID 1389558 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6].[C:17](Cl)(=[O:19])[CH3:18]>C(Cl)Cl>[C:17]([C:11]1[CH:10]=[C:9]([C:5]([CH3:6])([CH3:7])[CH3:8])[CH:14]=[CH:13][C:12]=1[OH:15])(=[O:19])[CH3:18].[C:17]([C:13]1[CH:14]=[C:9]([C:5]([CH3:8])([CH3:6])[CH3:7])[CH:10]=[CH:11][C:12]=1[O:15][CH3:16])(=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 94750p-tert-ButylanisoleHCID 6451240Aluminum(III) Chloride

Product 2

HCID 2630921-(5-Tert-butyl-2-hydroxyphenyl)ethan-1-oneHCID 13759988HCID 13759988, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
20 °C

Procedure

To 7.40 g of aluminum chloride suspended in 100 ml of methylene chloride were added, under nitrogen, 8.20 g of 4-tert-butylanisole (prepared in Reference Example 1) dissolved in 50 ml of methylene chloride at 0° C. followed by dropwise addition of 3.92 ml of acetyl chloride dissolved in 50 ml of methylene chloride at the same temperature. The mixture was stirred at 20° C. for 30 minutes. The reaction mixture was concentrated at reduced pressure and poured into 200 ml of ice-water and extracted with diethyl ether. The extract was washed with water and saturated brine successively, dried over magnesium sulfate anhydride and concentrated at reduced pressure. The residue was chromatographed on silica gel column using a mixed solvent of methylene chloride and cyclohexane (1:2) as an eluting agent to give 5.30 g of the title compound and 3.79 g of 2-acetyl-4-tert-butylanisole. The physical properties of each compound are as follows.

Workup

  1. additionwere added, under nitrogen
  2. concentrationThe reaction mixture was concentrated at reduced pressure
  3. additionpoured into 200 ml of ice-water
  4. extractionextracted with diethyl ether
  5. washThe extract was washed with water and saturated brine successively
  6. dry with materialdried over magnesium sulfate anhydride
  7. concentrationconcentrated at reduced pressure
  8. customThe residue was chromatographed on silica gel column

Sources & evidence

ORD record
ord-0f0028d4dd42489e89ef36fcffb100e6
Source dataset
uspto-grants-1981_01
Patent number
US04245099

Reaction notes

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