2-(benzyloxy)-4-nitrophenol synthesis
- Product Name:2-(benzyloxy)-4-nitrophenol
- CAS Number:50352-33-5
- Molecular formula:C13H11NO4
- Molecular Weight:245.23
75167-86-1
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Yield:50352-33-5 99%
Reaction Conditions:
Stage #1: 2-(benzyloxy)-1-methoxy-4-nitrobenzenewith sodium hydroxide in dimethyl sulfoxide at 100; for 5 h;
Stage #2: with hydrogenchloride in water;dimethyl sulfoxide; pH=1;Cooling with ice;
Steps:
1.B
A 200 mL round bottomed flask is charged with 2 -(ben? )-l -4- nitrobenzene ( 10.00 g, 38.6 mmol) and DMSO (30 mL). To the stirred suspension is added NaOH (I O N, 10 mL, 1 OO mmol). and the mixture is heated to 100 0C for 5 h. The solution is cooled to rt, and immersed in a water ice bath, and water (30 mL) is added to the solution. The pH is adjusted to ~1 by addition of concentrated HCl (10 mL, 121 mmol). The solution is extracted once with toluene (80 mL). The organic phase is washed successively w ith water (20 mL) and brine (20 mL), and evaporated to dryness yielding 9.37 g (99%) of the title compound as a yellow solid. LCMS (Standard Method); 2.70 min. 268 (M+Na) !H NMR (300 MHz, CDCl1) 5 7.92-7.86 (m, 2H), 7.45-7.41 (m, 5H). 7.00 (d, J = 8.8 Hz, IH). 5.20 (s, 2H).
References:
WO2008/118935,2008,A1 Location in patent:Page/Page column 33-34
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