1-Butanol → 3-(Ethylhydroxyphosphinyl)-2-methylpropionic acid

HRID 1028256ノート

反応式

HRID 1028256 の反応式
[CH2:1]([OH:5])[CH2:2][CH2:3]C.[OH-].[Na+].[CH2:8]([P:10]([CH2:17]C(C#N)C)(=[O:16])[O:11]CCCC)[CH3:9].S(=O)(=O)(O)[OH:23]>O>[CH2:8]([P:10]([OH:11])([CH2:17][CH:2]([CH3:3])[C:1]([OH:5])=[O:23])=[O:16])[CH3:9]

参加物

6

反応物 4

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 86657307Butyl ethyl(2-cyano-2-methylethyl)phosphinate

生成物 1

HCID 462165003-(Ethylhydroxyphosphinyl)-2-methylpropionic acid収率 96%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
120 °C

実験手順

A stirred apparatus is initially charged with 150 g of butanol, 65 g of water, 150 g (3.75 mol) of sodium hydroxide and 271 g (1.25 mol) of butyl ethyl(2-cyano-2-methylethyl)phosphinate (produced as in Example 9). The efficiently stirred mixture was heated to about 120° C. and reacted at that temperature for about 8 hours. Then, 250 ml of water were added and the butanol was removed from the reaction mixture by distillation. Following the addition of a further 500 ml of water, the mixture was neutralized by addition of about 184 g (1.88 mol) of concentrated sulfuric acid. The water is then distilled off in vacuo. The residue is taken up in tetrahydrofuran and extracted. The insoluble salts are filtered off. The solvent of the filtrate is removed in vacuo and the residue is recrystallized from acetone to obtain 216 g (96% of theory) of 3-(ethylhydroxyphosphinyl)-2-methylpropionic acid as a solid material.

後処理

  1. customreacted at that temperature for about 8 hours
  2. customthe butanol was removed from the reaction mixture by distillation
  3. additionthe addition of a further 500 ml of water
  4. distillationThe water is then distilled off in vacuo
  5. extractionextracted
  6. filtrationThe insoluble salts are filtered off
  7. customThe solvent of the filtrate is removed in vacuo
  8. customthe residue is recrystallized from acetone

出典と根拠

ORDレコード
ord-fb97843e7a80471d932647c9b254262b
出典データセット
uspto-grants-2014_05
特許番号
US08735477B2

反応ノート

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