Diethyl chlorophosphate → 2-Tert-butyl-4-methylphenyl diethyl phosphate

HRID 1403990ノート

反応式

HRID 1403990 の反応式
[H-].[Na+].[C:3]([C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[OH:14])([CH3:6])([CH3:5])[CH3:4].[CH2:15]([O:17][P:18](Cl)(=[O:22])[O:19][CH2:20][CH3:21])[CH3:16]>C1COCC1>[P:18]([O:19][CH2:20][CH3:21])([O:17][CH2:15][CH3:16])([O:14][C:8]1[CH:9]=[CH:10][C:11]([CH3:13])=[CH:12][C:7]=1[C:3]([CH3:6])([CH3:5])[CH3:4])=[O:22]

参加物

5

反応物 3

HCID 13139Diethyl chlorophosphateHCID 170042-tert-Butyl-4-methylphenolHCID 24758Sodium hydride

生成物 1

HCID 591293942-Tert-butyl-4-methylphenyl diethyl phosphate収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a suspension of NaH (60% in mineral oil, 8.4 g, 0.21 mol) in THF (200 mL) was added dropwise a solution of 2-tert-butyl-4-methylphenol (33 g, 0.20 mol) in THF (100 mL) at 0° C. The mixture was stirred at 0° C. for 15 min and then phosphorochloridic acid diethyl ester (37 g, 0.2.1 mol) was added dropwise at 0° C. After addition, the mixture was stirred at ambient temperature for 30 min. The reaction was quenched with sat. NH4Cl (300 mL) and then extracted with Et2O (350 mL×2). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and then evaporated under vacuum to give 2-tert-butyl-4-methylphenyl diethyl phosphate (contaminated with mineral oil) as a colorless oil (60 g, 100%), which was used directly in the next step.

後処理

  1. additionAfter addition
  2. stirringthe mixture was stirred at ambient temperature for 30 min
  3. customThe reaction was quenched with sat. NH4Cl (300 mL)
  4. extractionextracted with Et2O (350 mL×2)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated under vacuum

出典と根拠

ORDレコード
ord-e6d6456a30a64792890f6f5ce5c7b308
出典データセット
uspto-grants-2014_12
特許番号
US08912199B2

反応ノート

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