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

HRID 404346Notes

Reaction equation

HRID 404346 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>[CH3:7][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]

Participants

5

Reactant 3

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

Product 1

HCID 137241451-(3-Tert-butyl-4-hydroxyphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-45 °C

Procedure

To a dry, round bottom flask was added aluminum chloride (4.402 g, 33.0 mmol). The flask was then cooled to −45° C. After 10 minutes, dry toluene (80 mL) was added followed by dropwise addition of 2-tert-butylphenol (5.00 mL, 32.7 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA). The mixture was stirred and maintained at −4° C. After 1.5 hours, acetyl chloride (2.40 mL, 33.8 mmol) was carefully added dropwise. The mixture was allowed to warm to room temperature and monitored with TLC and LC-MS. After 18 hours, the mixture was slowly poured onto crushed ice. This mixture was stirred at room temperature and the crystals were collected by filtration. The light yellow solid was identified as T17.1 (4.2589 g, 68%). MS ESI (pos.) m/e: 193.1 (M+H)+.

Workup

  1. temperaturemaintained at −4° C
  2. waitAfter 1.5 hours
  3. temperatureto warm to room temperature
  4. waitAfter 18 hours
  5. additionthe mixture was slowly poured
  6. customonto crushed ice
  7. stirringThis mixture was stirred at room temperature
  8. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-79d1bc3808f145d7a76551d7208413c7
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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