ChemicalBook CAS DataBase List 4-Benzyloxy-5-methoxy-2-nitrotoluene

4-Benzyloxy-5-methoxy-2-nitrotoluene synthesis

5synthesis methods

Product Name:4-Benzyloxy-5-methoxy-2-nitrotoluene
CAS Number:121086-26-8
Molecular formula:C15H15NO4
Molecular Weight:273.28

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Yield: 95%

Reaction Conditions:

with nitric acid;acetic acid at 4 - 6; for 3 h;

Steps:

2 Step 2-1-Benzyloxy-2-methoxy-4-methyl-5-nitro-benzene
A stirred mixture of 1-benzyloxy-2-methoxy-4-methyl-benzene (17.5 g, 76.6 mmol) in HOAc (60 mL) was cooled to 4-6° C. and a mixture of concentrated HNO₃(49.0 g, 778 mmol) in HOAc (17 mL) was added dropwise. The reaction mixture was stirred at 4-6° C. for 3 hours. On completion, the reaction mixture was poured into 100 mL of an ice-H₂O mixture. The mixture was filtered and the solid precipitate was washed with water. The solid was dried in vacuo to give the title compound (20.0 g, 95% yield) as a yellow solid. ¹H NMR (400 MHz, DMSO-d₆) δ 7.73 (s, 1H), 7.49-7.33 (m, 5H), 7.09 (s, 1H), 5.17 (s, 2H), 3.90 (s, 3H), 2.54 (s, 3H).

References:

Kymera Therapeutics, Inc.;Mainolfi, Nello;Ji, Nan;Kluge, Arthur F.;Weiss, Matthew M.;Zhang, Yi US2019/192668, 2019, A1 Location in patent:Paragraph 2654; 2656