Cyclohexanone → Pentamethylbenzoic acid

HRID 903663ノート

反応式

HRID 903663 の反応式
[CH3:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([CH3:10])[C:5]([CH3:11])=[C:4]([CH3:12])[C:3]=1[CH3:13].C1(=[O:20])CCCCC1>C(O)(=O)C.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[CH3:1][C:2]1[C:7]([C:8]([OH:20])=[O:9])=[C:6]([CH3:10])[C:5]([CH3:11])=[C:4]([CH3:12])[C:3]=1[CH3:13]

参加物

5

反応物 2

HCID 7967CyclohexanoneHCID 263712Pentamethylbenzaldehyde

生成物 1

HCID 75236Pentamethylbenzoic acid収率 78.8%

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 6277Cobalt diacetate触媒

実験手順

To a flask equipped with a stirrer, oxygen inlet and condenser were added pentamethylbenzaldehyde (12.0 g, 68 mmol), 40 mL (0.387 mol) of cyclohexanone and 6 mg of cobalt (II) acetate dissolved in several drops of acetic acid. Oxygen was bubbled in while the solution was stirred rapidly and heated at 50° for 4 hours. The solution was mixed with 100 mL of cyclohexane and the mixture was extracted with 100 mL of 6% aqueous sodium bicarbonate solution. The aqueous layer was separated and the organic layer was washed with 50 mL of water. The combined aqueous layers were acidified with concentrated hydrochloric acid. The white crystalline solid product was collected by filtration, washed with water and air dried. A total of 10.3 g (78% yield) of pentamethylbenzoic acid was obtained: mp 202°-206°.

後処理

  1. customTo a flask equipped with a stirrer, oxygen inlet and condenser
  2. customOxygen was bubbled in while the solution
  3. temperatureheated at 50° for 4 hours
  4. additionThe solution was mixed with 100 mL of cyclohexane
  5. extractionthe mixture was extracted with 100 mL of 6% aqueous sodium bicarbonate solution
  6. customThe aqueous layer was separated
  7. washthe organic layer was washed with 50 mL of water
  8. filtrationThe white crystalline solid product was collected by filtration
  9. washwashed with water and air
  10. customdried

出典と根拠

ORDレコード
ord-424d1dd4d82e4c1db1abb8c1365fc0fb
出典データセット
uspto-grants-1980_10
特許番号
US04228302

反応ノート

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