Sulfur Dioxide → 3-Chloro-5-tert. butyl-4-hydroxybenzyl-phosphonic acid diethyl ester

HRID 616814

反応式

HRID 616814 の反応式
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:13]([OH:20])=[C:12](C(C)(C)C)[CH:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].S(Cl)([Cl:28])(=O)=O.S(=O)=O>C(Cl)(Cl)(Cl)Cl.N1C=CC=CC=1>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:13]([OH:20])=[C:12]([Cl:28])[CH:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

参加物

6

反応物 3

HCID 1119Sulfur DioxideHCID 24648Sulfuryl chlorideHCID 70421Diethyl ((3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl)methyl)phosphonate

生成物 1

HCID 867354993-Chloro-5-tert. butyl-4-hydroxybenzyl-phosphonic acid diethyl ester

試薬・触媒・溶媒 2

HCID 1049Pyridine触媒HCID 5943Carbon Tetrachloride溶媒

反応条件

温度
0 °C

実験手順

71.2 g of 3,5-di-tert. butyl-4-hydroxybenzyl-phosphonic acid diethyl ester are dissolved in 200 ml of carbon tetrachloride. After addition of a few drops of pyridine, 40.5 g of sulphuryl chloride are added dropwise, with stirring, at about 0° C in the course of 45 minutes. The reaction mixture is then further stirred for 10 hours at room temperature, in the course of which the formation of sulphur dioxide is observed. After the reaction is terminated, the solvent is removed as far as possible completely in vacuo. The semi-crystalline residue is digested with water and washed neutral and finally recrystallised from aqueous isopropanol in order to purify it. Instead of isopropanol it is also possible to use ethylene glycol monomethyl ether. Toluene is also suitable for effecting recrystallisation, but the crude product must in this case be freed from water beforehand. The 3-chloro-5-tert. butyl-4-hydroxybenzyl-phosphonic acid diethyl ester is obtained in the form of colourless crystals (stabiliser 1) with a melting point of 116° C.

後処理

  1. additionare added dropwise
  2. customAfter the reaction is terminated
  3. customthe solvent is removed as far as possible completely in vacuo
  4. washwashed neutral
  5. customfinally recrystallised from aqueous isopropanol in order
  6. customto purify it
  7. customrecrystallisation

出典と根拠

ORDレコード
ord-990654cce92842b785073a598741315f
出典データセット
uspto-grants-1978_02
特許番号
US04076690

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