Methanol → Diphenyl methylphosphonate

HRID 1680804ノート

反応式

HRID 1680804 の反応式
[P:1]([O:16]C1C=CC=CC=1)([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CO.[C:25]1(O)C=CC=CC=1.C1(OC)C=CC=CC=1>CI>[CH3:25][P:1](=[O:16])([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 887MethanolHCID 996PhenolHCID 7519AnisoleHCID 7540Triphenyl phosphite

生成物 1

HCID 82027Diphenyl methylphosphonate収率 92%

試薬・触媒・溶媒 1

HCID 6328Methyl iodide触媒

実験手順

A reactor fitted with an efficient condenser, thermometer, mechanical stirrer and side-arm addition funnel was charged with 1552 g (5.0 mol) of triphenyl phosphite. The reactant was placed under a nitrogen blanket and heated to reflux. A solution of 5.0 g of methyl iodide in 160 g (5.1 mol) of methanol was then slowly added over a two hour period. Throughout the addition, the temperature of the reactor contents was maintained within the 200°-250° C. range. One further hour at 215° C. proved sufficient for the reaction to reach completion. Subsequently, as aspirator vacuum distillation removed 468 g (5.0 mol) of phenol containing a small amount of anisole. Thereafter, a high vacuum distillation recovered 1150 g (4.6 mol, 92% yield) of diphenyl methylphosphonate. Glc analysis using a 6 foot column packed with 10% OV-101 on chromosorb W, was employed to monitor the progress of both the reaction and distillation. The s:p signal for the product appeared at -24.0 ppm. Proton nmr signals were seen at τ8.36 (3H, doublet, J=18 HZ, CH3P) and τ2.9-2.5 (10H, multiplet, phenyl).

後処理

  1. customA reactor fitted with an efficient condenser
  2. additionthermometer, mechanical stirrer and side-arm addition funnel
  3. temperatureheated to reflux
  4. additionThroughout the addition
  5. temperaturethe temperature of the reactor contents was maintained within the 200°-250° C. range
  6. customOne further hour at 215° C. proved sufficient for the reaction
  7. distillationSubsequently, as aspirator vacuum distillation
  8. distillationThereafter, a high vacuum distillation

出典と根拠

ORDレコード
ord-ada3a354c1484421b531995e9e87b910
出典データセット
uspto-grants-1981_06
特許番号
US04276234

反応ノート

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