2,4-Di-tert-butylphenol → Phosphoric acid 2,4-di-tert-butyl-phenyl ester diethyl ester

HRID 2189696Notes

Reaction equation

[H-].[Na+].[C:3]([C:7]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=[CH:9][C:8]=1[OH:17])([CH3:6])([CH3:5])[CH3:4].[CH2:18]([O:20][P:21](Cl)(=[O:25])[O:22][CH2:23][CH3:24])[CH3:19]>C1COCC1>[CH2:18]([O:20][P:21](=[O:25])([O:22][CH2:23][CH3:24])[O:17][C:8]1[CH:9]=[CH:10][C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:12][C:7]=1[C:3]([CH3:6])([CH3:5])[CH3:4])[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of NaH (60% in mineral oil, 6.99 g, 174.7 mmol) in THF (350 mL) was added dropwise a solution of 2,4-di-tert-butylphenol (35 g, 169.6 mmol) in THF (150 mL) at 0° C. The mixture was stirred at 0° C. for 15 min and then phosphorochloridic acid diethyl ester (30.15 g, 174.7 mmol) was added dropwise at 0° C. After addition, the mixture was stirred at this temperature for 15 min. The reaction was quenched with sat. NH4Cl (300 mL). The organic layer was separated and the aqueous phase was extracted with Et2O (350 mL×2). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum to give crude phosphoric acid 2,4-di-tert-butyl-phenyl ester diethyl ester as a yellow oil (51 g, contaminated with some mineral oil), which was used directly in the next step.

Workup

additionAfter addition
stirringthe mixture was stirred at this temperature for 15 min
customThe reaction was quenched with sat. NH4Cl (300 mL)
customThe organic layer was separated
extractionthe aqueous phase was extracted with Et2O (350 mL×2)
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-e30b2ee976774874b04a3b0c475746c3
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324242B2

Reaction notes

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