Acetyl chloride → Phenol, 4-ethyl-, 1-acetate

HRID 2170710Notes

Reaction equation

HRID 2170710 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)[CH3:2].[C:10](Cl)(=[O:12])[CH3:11]>C(Cl)Cl>[C:10]([O:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=1)(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 312424-Ethylphenol

Product 1

HCID 76731Phenol, 4-ethyl-, 1-acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-ethylphenol (3.38 g, 27.67 mmol) in DCM (50 mL) in an ice bath was added TEA (7.2 mL, 55.34 mmol), followed by the dropwise addition of acetyl chloride (2.2 mL, 30.44 mmol). The mixture was stirred at room temperature for 30 min. The reaction mixture was quenched with water (40 mL) and extracted with DCM (3×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure and purified by silica gel chromatography to obtain the title compound.

Workup

  1. customThe reaction mixture was quenched with water (40 mL)
  2. extractionextracted with DCM (3×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-22e15d79b1664cc886c809c1038ca568
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

Loading…