Acetyl chloride → AG-G-97635

HRID 2103001Notes

Reaction equation

HRID 2103001 reaction equation
[CH3:1][C:2]1[C:3]([OH:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([CH:8]=1)[OH:7].[C:12](Cl)(=[O:14])[CH3:13].[C:16](OCC)(=[O:18])[CH3:17]>C1(C)C=CC=CC=1.CCCCCC>[C:12]([O:7][C:6]1[CH:8]=[C:2]([CH3:1])[C:3]([O:11][C:16](=[O:18])[CH3:17])=[C:4]([CH3:10])[C:5]=1[CH3:9])(=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 6367Acetyl chloride2×HCID 8857Ethyl AcetateHCID 12785Trimethylhydroquinone

Product 1

HCID 344608AG-G-97635

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

To a solution of trimethylhydroquinone (30 g) in 200 mL of toluene was added acetyl chloride (28 mL). The reaction mixture was allowed to reflux for 2 hours. More acetyl chloride (28 mL) was added, and the reaction mixture was allowed to reflux for additional 2 hours. After the reaction was complete as indicated by TLC (20% ethyl acetate in hexane), the reaction was allowed to cool down and concentrated in vacuo. Recrystallization of the resulting residue from ethyl acetate and hexane gave 42.3 g of 2,3,5-trimethyl-1,4-phenylene diacetate as a white solid.

Workup

  1. temperatureto reflux for 2 hours
  2. temperatureto reflux for additional 2 hours
  3. temperatureto cool down
  4. concentrationconcentrated in vacuo
  5. customRecrystallization of the resulting residue from ethyl acetate and hexane

Sources & evidence

ORD record
ord-87876140bc8149cabe2757a28129db87
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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