Acetyl chloride → 1-(3-Tert-butyl-4-hydroxyphenyl)ethanone

HRID 2223761Notes

Reaction equation

HRID 2223761 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])([CH3:8])([CH3:7])[CH3:6].[C:16](Cl)(=[O:18])[CH3:17]>C1(C)C=CC=CC=1>[C:5]([C:9]1[CH:14]=[C:13]([C:16](=[O:18])[CH3:17])[CH:12]=[CH:11][C:10]=1[OH:15])([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 69232-Tert-ButylphenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 137241451-(3-Tert-butyl-4-hydroxyphenyl)ethanoneYield 76.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Aluminum chloride (44.4 g, 333 mmol) was cooled to −45° C., and toluene (1.25 L) was added followed by 2-tert-Butylphenol (50.0 g, 333 mmol). The sample was then stirred for 2 hours. In addition, acetyl chloride (26.1 g, 333 mmol) was added dropwise, followed by 2.5 hours of stirring. The reaction solution was added dropwise to ice-cold water (250 mL), and then this was stirred at room temperature. Crystals were collected by filtration and dried under reduced pressure (50° C.) to give 48.7 g of the subject compound as white crystals (yield: 76.1%, HPLC purity: 99.8%).

Workup

  1. waitfollowed by 2.5 hours
  2. stirringof stirring
  3. stirringthis was stirred at room temperature
  4. filtrationCrystals were collected by filtration
  5. customdried under reduced pressure (50° C.)

Sources & evidence

ORD record
ord-393e540ea72042f99f2747a2fafa6baa
Source dataset
uspto-grants-2008_05
Patent number
US07375236B2

Reaction notes

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