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

HRID 1847486Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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, 0.21 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.

Workup

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

Sources & evidence

ORD record: ord-a91104a4214c4e5992e8d5ed7d7c1a03
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952050B2

Reaction notes

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