Sodium Hydroxide → gamma-Propanol

HRID 370744

反応式

HRID 370744 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18](OC)=[O:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>CCOCC>[C:12]([C:9]1[CH:8]=[C:7]([CH2:16][CH2:17][CH2:18][OH:19])[CH:6]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:10]=1[OH:11])([CH3:15])([CH3:13])[CH3:14]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 62603Methyl di-t-butyl hydroxyhydrocinnamateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 169766gamma-Propanol収率 95.5%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A solution of methyl 3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate (117 g, 0.4 mol) in 200 ml of anhydrous ether was added dropwise to a mixture of lithium aluminum hydride (17 g, 0.45 mol) and anhydrous ether (800 ml) under an inert atmosphere with ice-water cooling. After the addition was completed, the reaction mixture was heated at reflux temperature for one hour, then cooled to room temperature. To the cooled mixture was added dropwise 80 ml of 3% sodium hydroxide aqueous solution with vigorous stirring and with ice-water cooling. After the addition was completed, the mixture was stirred at room temperature for 30 minutes. A white precipitate was separated by filtration and washed with ether. The filtrate and washings were combined and evaporated. The residue was vacuum distilled to give 101 g (95%) of the product.

後処理

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux temperature for one hour
  4. additionAfter the addition
  5. customA white precipitate was separated by filtration
  6. washwashed with ether
  7. customevaporated
  8. distillationdistilled

出典と根拠

ORDレコード
ord-4e59ee1e546a42349ecf7b547734f3b8
出典データセット
uspto-grants-1985_07
特許番号
US04528311

関連ノート

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