ChemicalBook CAS DataBase List 2-(HYDROXYMETHYL)-4-NITROBENZENOL

2-(HYDROXYMETHYL)-4-NITROBENZENOL synthesis

11synthesis methods

Product Name:2-(HYDROXYMETHYL)-4-NITROBENZENOL
CAS Number:39224-61-8
Molecular formula:C7H7NO4
Molecular Weight:169.13

96-97-9 Synthesis

96-97-9
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39224-61-8
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$37.00/500mg

Yield: 100%

Reaction Conditions:

with borane-THF in tetrahydrofuran at 0 - 20; for 18.0833 h;Inert atmosphere;

Steps:

8.1 [00126] Step One. 2-(Hydroxymethyl)-4-nitrophenol (D2):
To a borane THF complex solution (1 M, 10.9 mL, 10.9 mmol) was added a solution of compound Di (1.00 g, 5.46 mmol) in anhydrous THF (50 mL) dropwise over 5 mm at 0 °C under nitrogen. After theaddition was completed, the reaction mixture was warmed to ambient temperature and stirred for 18 h. After this time, the reaction was quenched by slow addition of 1 N hydrochloric acid (25 mL) at 0 °C. The resulting mixture was stirred at ambient temperature for 2 h and then extracted with tert-butylmethyl ether (3 x 50 mL). The combined extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to afford compound D2 (0.923 g, quant.) as a yellow solid: ‘H NMR (300 MHz, DMSO-d6) 11.14 (s, 1H), 8.21 (d, J = 2.9 Hz, 1H), 8.03 (dd, J= 8.9, 3.0 Hz, 1H), 6.94 (d, J= 8.9 Hz, 1H), 5.36 (br s, 1H), 4.51 (s,2H).

References:

WARRELL, Raymond P., Jr.;PIWINSKI, John J. WO2016/118611, 2016, A1 Location in patent:Paragraph 00126