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

HRID 1387196ノート

反応式

HRID 1387196 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 31062832-Benzoyl-4-tert-butylbenzoic acid収率 54%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1049897583fe4dec8a47cc105ffafcdf
出典データセット
uspto-grants-2001_07
特許番号
US06268072B1

反応ノート

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