Water → 3-(2-Methylbenzyl)-butanone

HRID 231760

反応式

HRID 231760 の反応式
[OH-].[K+].O.C1OCCOCCOCCOCCOCCOC1.[CH3:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25]Cl.[CH2:31]([C:33]([CH3:35])=[O:34])[CH3:32]>C1(C)C=CC=CC=1>[CH3:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25][CH:31]([CH3:32])[C:33](=[O:34])[CH3:35]

参加物

7

反応物 5

HCID 962WaterHCID 6569Methyl Ethyl KetoneHCID 11093alpha-Chloro-o-xyleneHCID 14797Potassium HydroxideHCID 2855718-Crown-6

生成物 1

HCID 178044723-(2-Methylbenzyl)-butanone収率 23.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
85 °C

実験手順

56 g of KOH, 56 ml of water, 10 g of 18-crown-6 and 5 g of KI were warmed to 75° C. with 200 ml of toluene with exclusion of air. A mixture of 100 g of 2-methylbenzyl chloride and 100 g of methyl ethyl ketone was added dropwise over 30 minutes with vigorous stirring, and the mixture was stirred at 85° C. for 11 hours. The phases were then separated, and the organic layer was washed by shaking with water and distilled through a short packed column. After removing the solvent and the preliminary fraction, 29 g of 3-(2-methylbenzyl)-butanone were obtained at 54°-55° C./0.07 mbar. 25 g of this compound was stirred with 3 g of NaBH4 in 100 ml of ethanol, initially for 2 hours at 25° C., then for a further 2 hours at the reflux temperature. After the reducing agent and solvent had been removed, the reaction product was distilled through a short Vigreux column. 15.5 g of 3-methyl-4-(2-methylphenyl)-butan-2-ol were obtained from 64°-67° C./0.07 mbar.

後処理

  1. additionwas added dropwise over 30 minutes with vigorous stirring
  2. customThe phases were then separated
  3. washthe organic layer was washed
  4. stirringby shaking with water
  5. distillationdistilled through
  6. customAfter removing the solvent

出典と根拠

ORDレコード
ord-a685bd66646b401d895a9495129f8911
出典データセット
uspto-grants-1989_07
特許番号
US04849401

関連ノート

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