Reaction #2329028

ord-8044212375034425a9fa8f3f91130488

Reaction equation

Cl
hydrochloric acid
CC(C)(C)c1ccc2c(c1)C(=O)OC2=O
4-t-butylphthalic anhydride
CC(C)(C)c1ccccc1
t-butylbenzene
[Al+3].[Cl-].[Cl-].[Cl-]
Aluminum chloride
→
CC(C)(C)c1ccc(C(=O)c2cc(C(C)(C)C)ccc2C(=O)O)cc1
benzoic acid
Yield 64.0%
CC(C)(C)c1ccc(C(=O)c2cc(C(C)(C)C)ccc2C(=O)O)cc1
4-t-butyl-2-[4-t-butylbenzoyl)benzoic acid
Yield 64.0%

Reactants

Cl
hydrochloric acid
CC(C)(C)c1ccc2c(c1)C(=O)OC2=O
4-t-butylphthalic anhydride
CC(C)(C)c1ccccc1
t-butylbenzene
[Al+3].[Cl-].[Cl-].[Cl-]
Aluminum chloride

Reagents

None

Solvents

CC(Cl)Cl
dichloroethane

Conditions

Temperature
0°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONAdded into a 500 ml three-necked flask under the environment of argon
  2. 2
    workup.ADDITIONAfter the addition, they
  3. 3
    OtherAfter the reaction, ice
  4. 4
    workup.ADDITIONwas added gradually
  5. 5
    FiltrationAfter the precipitates were filtered
  6. 6
    Washthey were thoroughly washed

Procedure

Added into a 500 ml three-necked flask under the environment of argon were 4-t-butylphthalic anhydride 36 g (176 mmole), t-butylbenzene 27 g (200 mmole) and dichloroethane 100 ml. The mixture was cooled to 0° C. Aluminum chloride 56 g (420 mmole) was added gradually to them. After the addition, they were stirred at room temperature overnight. After the reaction, ice was added gradually followed by the addition of concentrated hydrochloric acid. After the precipitates were filtered, they were thoroughly washed to give the benzoic acid substance 32 g (yield 64%, white powder).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07670506B1uspto-grants-2010_03