Toluene → 1-(3-Tert-butyl-4-hydroxyphenyl)ethanone

HRID 244333Notes

Reaction equation

HRID 244333 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C1(C)C=CC=CC=1.[C:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[OH:22])([CH3:15])([CH3:14])[CH3:13].[C:23](Cl)(=[O:25])[CH3:24]>O>[C:12]([C:16]1[CH:21]=[C:20]([C:23](=[O:25])[CH3:24])[CH:19]=[CH:18][C:17]=1[OH:22])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 1140TolueneHCID 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 962WaterSolvent

Procedure

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

Workup

  1. stirringstirred for 2.5 hours
  2. customThe resultant reaction solution
  3. additionwas added to ice-
  4. stirringstirred at room temperature
  5. filtrationCrystals were collected by filtration
  6. customdried under reduced pressure (50° C.)

Sources & evidence

ORD record
ord-13a618abd20544cb98fea892e5ee6d6d
Source dataset
uspto-grants-2014_02
Patent number
US08658620B2

Reaction notes

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