1,4-DIBENZYLOXY-2-NITROBENZENE

Nitric acid (70percent) (19.5 ml, 437.4 mmol, 2.0 equiv) was added slowly to a suspensionof hydroquinol 2 (63.5 g, 218.7 mmol, 1.0 equiv) in glacial acetic acid(400 ml) at 0 C. The solutionwas stirred at 0 C for 3 h, poured intowater (w1500 ml) and the resulting precipitate filtered off. Theprecipitate was washed with water (1500 ml), dissolved in CHCl3(300 ml), dried over magnesium sulfate and concentrated undervacuum to give nitro compound 3 as a yellow solid. (73.04 g, 100percent).mp 80e81 C (lit.: 80e81 C44). dH (400 MHz, CDCl3): 7.49 (1H, d, J3.0, H3), 7.46e7.30 (10H, m, OCH2Ph), 7.12 (1H, dd, J9.2, 3.1 Hz, H5), 7.05 (1H, d, J9.2 Hz, H6), 5.18 (2H, s, CH2), 5.05 (2H, s, CH2). 13CNMR (101 MHz, CDCl3) d 152.30 (C), 146.39 (C), 135.97 (C), 135.88(C), 128.75 (CH), 128.70 (CH), 128.37 (CH), 128.22 (CH), 127.59 (CH), 127.15 (CH), 121.54 (CH), 117.24, 111.18 (CH), 72.10 (CH2), 70.94(CH2). IR (ATR cm1): 1520 (NO2), 1497 (CAr]CAr), 1341 (NO2). MS(ESI): 358 [(MNa), 100]. HRMS: 358.1034. C20H17NNaO4 requires358.1050. Spectroscopic data agree with lit.31General procedure: To a solution of phenol (1 mmol) in acetone (5 mL) wasadded silica supported Al(NO3)3·9H2O (1 mmol) and theresulting mixture stirred at room temperature. After completionof the reaction, as indicated by TLC, the reaction masswas filtered and the residue (silica) was washed with ethylacetate (2 5 mL). The filtrate and the washing were collectivelyconcentrated under reduced pressure, and the crudecompound was purified by column chromatography oversilica gel (100-200 mesh) to afford the pure ortho-nitro phenol(95percent) and para- nitro phenol (3percent).Add 1 mmol of 1, 4-dibenzyloxybenzene to the reaction flask, dissolve in 2 mL of dichloromethane, add 145 uL of t-butyl nitrite, stir at room temperature for 1 hour, and after the reaction, remove with a rotary evaporator. Removal of organic solvent, column chromatography to obtain the product nitro product, reaction yield 77percentTo a 100-mL round-bottom flask was placed a solution of 2-nitrobenzene-1, 4-diol (1 g, 6.45 mmol) in acetone (15 mL) then K2C03 (4.45 g, 32.20 mmol) and (bromomethyl)benzene (2.64 g, 15.48mmol) were added. Thereaction was stirred for 10 h at rt, filtered, and concentrated under reduced pressure affording1.302 g (60percent) of the title compound as a yellow solid.

Molecular Weight:335.4
XLogP3:4.7
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:335.11575802
Monoisotopic Mass:335.11575802
Topological Polar Surface Area:64.3
Heavy Atom Count:25
Complexity:399
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes