Hydrochloric Acid → 2-Benzoyl-4-tert-butylbenzoic acid

HRID 1387196Notes

Reaction equation

HRID 1387196 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[O:13])[O:11][C:9](=[O:10])[C:8]2=[CH:14][CH:15]=1)([CH3:4])([CH3:3])[CH3:2].C([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(C)(C)C.Cl.[Al+3].[Cl-].[Cl-].[Cl-]>CCCCCC>[C:1]([C:5]1[CH:15]=[CH:14][C:8]([C:9]([OH:11])=[O:10])=[C:7]([C:12](=[O:13])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 7366Tert-ButylbenzeneHCID 1229304-tert-Butylphthalic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 31062832-Benzoyl-4-tert-butylbenzoic acidYield 54%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
70 °C

Procedure

4-t-Butyl-phthalic anhydride (36.0 g; 176 mmol) and t-butyl benzene were placed under nitrogen in a 3-neck round-bottom flask equipped with a condenser. The condenser was attached to a water-gas trap for HCl released during the reaction. AlCl3 (56.0 g; 420 mmol) was added in portions during which time the mixture turned dark brown. Stirring became difficult in the thick mixture. The reaction was heated at 70° C. for 1 h and then cooled to room temperature. Ice was added slowly to the flask followed by concentrated HCl solution. A large clump of solid stuck to the bottom of the flask. This was washed multiple times with water and then dissolved in CH2Cl2, washed with water, dried over Na2SO4 and concentrated to give an oily solid. Hexane was added and after sonication, a blue-white solid was collected by filtration. Drying gave product as white solid 32.0 g (54% yield). 1H NMR (CDCl3) δ (ppm): 1.33 (s, 18 H), 7.30 (d, J=8.0 Hz, 1H), 7.43 (d, J=8.3 Hz, 2H), 7.63-7.70 (m, 3H), 8.08 (s, 1H); 13C NMR (CDCl3): 30.98, 34.92, 125.36, 125.41, 127.78, 127.84, 128.02, 129.51, 129.60, 129.81, 134.56, 139.83, 152.94, 156.80, 170.80, 196.89.

Workup

  1. customequipped with a condenser
  2. customreleased during the reaction
  3. temperaturecooled to room temperature
  4. additionIce was added slowly to the flask
  5. washThis was washed multiple times with water
  6. dissolutiondissolved in CH2Cl2
  7. washwashed with water
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customto give an oily solid
  11. customafter sonication
  12. filtrationa blue-white solid was collected by filtration
  13. customDrying

Sources & evidence

ORD record
ord-1049897583fe4dec8a47cc105ffafcdf
Source dataset
uspto-grants-2001_07
Patent number
US06268072B1

Reaction notes

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