Hydrochloric Acid → 4-(2,2-Dimethylpropyl)benzoic acid

HRID 360001ノート

反応式

HRID 360001 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:9])[C:6](Cl)=O.[CH2:11]([C:16]1[CH:21]=[CH:20]C=[CH:18][CH:17]=1)[C:12]([CH3:15])([CH3:14])[CH3:13].Cl.[OH-:23].[Na+]>C(Cl)Cl.C(O)C.O>[CH2:11]([C:16]1[CH:21]=[CH:20][C:6]([C:5]([OH:9])=[O:23])=[CH:18][CH:17]=1)[C:12]([CH3:15])([CH3:14])[CH3:13]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 13877Benzene, (2,2-dimethylpropyl)-HCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 81670894-(2,2-Dimethylpropyl)benzoic acid

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a cooled suspension of 43.0 g of anhydrous aluminum chloride in 250 ml of methylene chloride was added 40.0 g of oxalyl chloride over a period of 25 minutes. The resulting mixture was stirred for 5 minutes and then 43.2 g of neopentylbenzene was added dropwise maintaining a temperature of 0°-5° C. over a period of 35 minutes. The dark red mixture was stirred at an ambient temperature and then heated slowly to reflux for 3 hours, cooled, and poured into a mixture of 250 g of ice and 188 ml of concentrated hydrochloric acid. The mixture was stirred for 1/2 hour, and two layers were separated. The aqueous layer was extracted with methylene chloride and the combined organic layers were evaporated to yield a brown oily residue. The residue was heated and stirred under reflux with 200 ml of 10N sodium hydroxide, 150 ml of water, and 250 ml of ethyl alcohol for 20 minutes, cooled, and the mixture was extracted with ether. The aqueous layer was acidified with concentrated hydrochloric acid and stirred for 1 hour. The solid was collected by filtration, washed with water, dissolved in ethyl acetate, the aqueous layer was discarded, dried and evaporated to yield a solid. The solid was crystallized from acetone to yield p-neopentylbenzoic acid as a beige solid, mp 191°-193° C.

後処理

  1. temperaturemaintaining a temperature of 0°-5° C. over a period of 35 minutes
  2. stirringThe dark red mixture was stirred at an ambient temperature
  3. temperatureheated slowly
  4. temperatureto reflux for 3 hours
  5. temperaturecooled
  6. stirringThe mixture was stirred for 1/2 hour
  7. customtwo layers were separated
  8. extractionThe aqueous layer was extracted with methylene chloride
  9. customthe combined organic layers were evaporated
  10. customto yield a brown oily residue
  11. temperatureThe residue was heated
  12. stirringstirred
  13. temperaturecooled
  14. extractionthe mixture was extracted with ether
  15. stirringstirred for 1 hour
  16. filtrationThe solid was collected by filtration
  17. washwashed with water
  18. dissolutiondissolved in ethyl acetate
  19. customdried
  20. customevaporated
  21. customto yield a solid
  22. customThe solid was crystallized from acetone

出典と根拠

ORDレコード
ord-4511576c9a8b4a4ab303a30e2ff0bf71
出典データセット
uspto-grants-1991_03
特許番号
US05003106

反応ノート

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