Hydrochloric Acid → 2-Hydroxy-5-methylbenzophenone

HRID 617670

反応式

HRID 617670 の反応式
CN(C)C1CCCCC1.[CH:10]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]([CH3:17])[CH:11]=1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[Cl-].[Cl-].[Al+3].Cl>ClC1C=CC=CC=1.O>[OH:16][C:15]1[CH:14]=[CH:13][C:12]([CH3:17])=[CH:11][C:10]=1[C:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:25]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 2879P-CresolHCID 7412Benzoyl chlorideHCID 7415N,N-DimethylcyclohexylamineHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 738512-Hydroxy-5-methylbenzophenone収率 81%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 7964Chlorobenzene溶媒

反応条件

温度
50 °C

実験手順

##STR19## 38 g (0.3 mol) of dimethylcyclohexylamine and 27 g (0.25 mol) of p-cresol in 150 ml of chlorobenzene were initially taken. 35.1 g (0.25 mol) of benzoyl chloride were added dropwise over one hour, the temperature increasing to 50° C. After cooling to room temperature, the suspension was added to 100 ml of water in order to separate off the dimethylcyclohexylamine hydrochloride. The organic phase was separated off and was dried by partial distillation. 33 g (0.25 mol) of aluminum trichloride were then added a little at a time at room temperature in the course of 30 minutes. During this procedure, the internal temperature increased to 50° C. The batch was stirred at 130° C. for about 10 hours until the evolution of HCl gas had ceased. After cooling to 60° C., the reaction mixture was poured onto ice water. The phases were separated and the aqueous phase was extracted twice with chlorobenzene. The combined organic phases were dried over magnesium sulfate and then evaporated down. 43 g (corresponding to a yield of 81%) of 2-hydroxy-5-methylbenzophenone were obtained. 25 g (0.12 mol) of the compound were then dissolved in 150 ml of methanol, and 4.1 g of sodium hydroxide in 30 ml of methanol were then added. The refluxing reaction mixture was stirred for 3 hours and then evaporated down in a rotary evaporator. 27 g (corresponding to a yield of 98%) of the title compound were obtained in the form of an orange solid.

後処理

  1. temperatureAfter cooling to room temperature
  2. customto separate off the dimethylcyclohexylamine hydrochloride
  3. customThe organic phase was separated off
  4. customwas dried by partial distillation
  5. temperatureDuring this procedure, the internal temperature increased to 50° C
  6. temperatureAfter cooling to 60° C.
  7. additionthe reaction mixture was poured onto ice water
  8. customThe phases were separated
  9. extractionthe aqueous phase was extracted twice with chlorobenzene
  10. dry with materialThe combined organic phases were dried over magnesium sulfate
  11. customevaporated down

出典と根拠

ORDレコード
ord-7ce948ef2a284e4eb65d3616528227b9
出典データセット
uspto-grants-1999_09
特許番号
US05951841

関連ノート

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