ChemicalBook CAS DataBase List DIETHYL(4-HYDROXYPHENYL)PHOSPHONATE

DIETHYL(4-HYDROXYPHENYL)PHOSPHONATE synthesis

11synthesis methods

Product Name:DIETHYL(4-HYDROXYPHENYL)PHOSPHONATE
CAS Number:28255-39-2
Molecular formula:C10H15O4P
Molecular Weight:230.2

Phosphonic acid, P-[4-(acetyloxy)phenyl]-, diethyl ester

25944-72-3
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28255-39-2
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Yield:28255-39-2 97%

Reaction Conditions:

Stage #1: diethyl p-acetoxyphenylphosphonatewith potassium hydroxide;water in tetrahydrofuran;methanol at 20; for 2 h;
Stage #2: with hydrogenchloride in dichloromethane;water;

Steps:

5

Preparation of p-Diethoxyphosphorylphenol (24). A mixture of 12.02 g (44.17 mmol) of 23 and 4.96 g (88.33 mmol) of KOH in 50 ml of methanol, 50 ml of tetrahydrofuran and 50 ml of water was stirred for 2 hours at RT. The solvents were removed under reduced pressure and the resulting oil treated with 100 ml of DCM and 100 ml of 2N HCl. The organic layer was separated, washed with 2N HCl (1 x 30 ml) , water (2 x 30 ml) , dried overMgSO₄ and evaporated under reduced pressure to yield 9.83 g (97%) of 24 as a colourless oil. ¹H NMR (CDCl₃, 25°C, 600MHz) ?57.66-7.60 (m, 2H, ArH), 7.02-6.97 (m, 2H, ArJi^"), 4.14- 4.01 (m, 4H, POCH₂), 1.30 (dt, 6H, CH₃, J = 6.0/0.6 Hz); ¹³C NMR (CDCl₃, 25°C, 151 MHz) ￡161.72 (d, ⁴Jp-C = 3.5 Hz), 133.74 (d, ²Jp-C = 11.6 Hz), 115.97 (d, ³J_P-C = 16.4 Hz), 115.65 (d, ¹Jp-_C = 197.4 Hz), 62.32 (d, ²J_P-_C - 5.3 Hz), 16.19 (d, ³Jp-_C = 6.5 Hz); ³¹P NMR (CDCl₃, 25°C, 243 MHz) ?520.66.