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

HRID 2098905Notes

Reaction equation

HRID 2098905 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 Aldrich). 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 T5.1 (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-c73911df5c474bffbdfad23e40c2c2ee
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

Loading…