Synthesis of 2-nitroanisole

Preparation of 2-nitroanisole

Preparation of 2-nitroanisole

Preparation of 2-nitroanisole

In an autoclave of 1-liter capacity, without stirrer, and heated by an oil bath, is placed 600 ml. dry methyl alcohol in which 23 grams of metallic sodium has previously been dissolved (reflux condenser), and to this is added 158 grams of pure o-nitrochlorobenzene (m.p. about 32°C; b.p. 243°). The autoclave is sealed and the heating is started. The temperature is raised to 120° over a period of 1 hour, held at this point for 3 hours, and finally held at 128° for 1 hour more. The pressure is 8 to 10 atmospheres. At the end of the reaction, the methyl alcohol is blown out through the valve into a good condenser. The recovered methyl alcohol can be used without purification in a subsequent run. The reaction product is removed from the autoclave, washing the latter out with hot water to remove the sodium chloride. The crude product is washed twice with five times its volume of hot water, separated, and distilled in vacuum. The yield is 136 grams, or 88 % of the theoretical amount. The product boils at 141° at 15 mm.

The fundamental processes of dye chemistry, by H. E. Fierz-David, 97-98, 1949

Preparation of 2-nitroanisole_

Preparation of 2-nitroanisole_

The 1 mole of 2-nitrophenol is treated rapidly with stirring, in a three-necked flask provided with a reflux condenser, stirrer, internal thermometer, and dropping funnel, with 1.25 mole of 10% sodium. With vigorous stirring, 1 mole of dimethyl sulfate is added in such a way that the temperature remains below 40° C (water cooling). To complete the reaction and to destroy unchanged dimethyl sulfate, the mixture is then heated for 30 min on a boiling water bath. After cooling, the organic layer is separated off and the aqueous solution is extracted several times with ether. The combined organic phases are washed with dilute sodium carbonate and then with water, dried with calcium chloride, and fractionated. Unchanged 2-nitrophenol can be recovered by acidifying the aqueous reaction solution and the wash water and extracting them with ether. The yield of 2-methylanisole is 50%, b.p. 273 °C; b.p. 133°C/11mm; m.p. 9-12 °C.

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 206-207, (1973)

IUPAC Name

1-methoxy-2-nitrobenzene

InChI

InChI=1S/C7H7NO3/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5H,1H3

InChI Key

CFBYEGUGFPZCNF-UHFFFAOYSA-N

Canonical SMILES

COC1=CC=CC=C1[N+](=O)[O-]

MeSH Synonyms

2-nitroanisole, o-nitroanisole, o-nitrophenyl methyl ether, ortho-nitroanisole

Depositor-Supplied Synonyms

2-Nitroanisole, 1-Methoxy-2-nitrobenzene, O-NITROANISOLE, 91-23-6, 2-Methoxynitrobenzene, Anisole, o-nitro-, 1-Nitro-2-methoxybenzene, Benzene, 1-methoxy-2-nitro-, o-Nitrophenyl methyl ether, 2-Methoxy-1-nitrobenzene, Benzene, methoxynitro-, NCI-C60388, 1-methoxy-2-nitro-benzene, ortho-Nitrobenzene methyl ether, CCRIS 2319, CHEBI:48722, HSDB 5186, CFBYEGUGFPZCNF-UHFFFAOYSA-N, NSC 5506, EINECS 202-052-1, SBB061020, AI3-00230, DSSTox_CID_962, DSSTox_RID_75890, DSSTox_GSID_20962, 29191-53-5, CAS-91-23-6, ortho-NITROANISOLE, o-methoxynitrobenzene, PubChem9645, 2-NITROANISOL, o-Nitro(methoxy)benzene, AC1L1NVY, UNII-ZRE7HLZ17K, ZRE7HLZ17K, ORTHO NITRO ANISOLE, ACMC-209r8j, substituted 2-nitroanisoles, o-Nitrobenzene methyl ether, NSC 5506 (Related), KSC205G9T, MLS002454428, SCHEMBL186551, 236284_ALDRICH, CHEMBL166415, CHEBI:48727, CTK1A5399, NSC5506, MolPort-001-783-081, HMS3039G04, LABOTEST-BB LTBB003009, LS-38, AC1Q2073, ACT10571, NSC-5506, ZINC1686985, Tox21_201984, Tox21_302981, ANW-39569, AR-1K7438, STL356493, ZINC01686985, AKOS000119961, AS04272, MCULE-1590319114, RTR-032946, UN 2730, NCGC00091551-01, NCGC00091551-02, NCGC00091551-03, NCGC00256425-01, NCGC00259533-01, AJ-29868, AK116686, AN-42552, CJ-27873, I744, OR001380, OR145899, SC-07299, SMR001372018, KB-173961, KB-204398, TR-032946, FT-0081673, FT-0613174, N0125, ST24038066, ST51047099, C19270, 3B4-0436, I01-6055, W-100313, UNII-A8BA06542K component CFBYEGUGFPZCNF-UHFFFAOYSA-N, InChI=1/C7H7NO3/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5H,1H, 35973-13-8

Removed Synonyms

Nitroanisole, C7H7NO3, CID7048, UN2730, Nitroanisole [UN2730] [Keep away from food], C005328, N02930000, N029300000, 54888-15-2

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