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

HRID 468418

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-cda5f69bd08b4247ab09d9f9d60f509c
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08623905B2

Linked notes

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