Synthesis of 2-nitrophenol

Preparation of 2-nitrophenol

Preparation of 2-nitrophenol

Preparation of 2-nitrophenol

A mixture of 94 grams of phenol and 20 ml. water is added dropwise to a obtained solution containing of 150 grams of sodium nitrate dissolved in 400 ml. water and 250 grams of concentrated sulfuric acid. Good stirring is maintained during the addition, and the temperature is kept below 20°C. Stirring is continued for 2 hours. The mother liquor is poured off from the tarry mixture of nitrophenols, and the tar is melted with 500 ml. water with the addition of enough chalk to make the mixture neutral to litmus. The wash water is poured off and the washing repeated. The crude ortho and para nitrophenols, freed from nitric acid, are subjected to steam distillation, using a condenser with a wide tube. About 40 grams of pure o-nitrophenol distills over. The residue in the distillation flask is cooled and filtered after standing for 24 hours. The precipitate is boiled with 1 liter of 2% hydrochloric acid and filtered through a fluted filter. The pure p-nitrophenol crystallizes from the filtrate in nearly white, long needles. The extraction can be repeated if necessary. The yield is about 40 grams each of the ortho-nitrophenol and para-nitrophenol isomers. It is bad practice to treat the crude nitrophenols with sodium hydroxide, as called for in some procedures, because the sodium hydroxide has an immediate resinifying action.

The fundamental processes of dye chemistry, by H. E. Fierz-David, 106-107, 1949

IUPAC Name

2-nitrophenol

InChI

InChI=1S/C6H5NO3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H

InChI Key

IQUPABOKLQSFBK-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

2-nitrophenol, 2-nitrophenol, ammonium salt, 2-nitrophenol, sodium salt, ortho-nitrophenol

Depositor-Supplied Synonyms

2-NITROPHENOL, o-Nitrophenol, 88-75-5, 2-Hydroxynitrobenzene, Phenol, 2-nitro-, o-Hydroxynitrobenzene, Phenol, o-nitro-, NITROPHENOL, ortho-nitrophenol, nitro phenol, o-Nitrofenol, 2-nitro-phenol, o-Nitrofenol [Czech], o-Nitrophenol (molten), CCRIS 2314, CHEBI:16260, HSDB 1133, IQUPABOKLQSFBK-UHFFFAOYSA-N, NSC 1552, EINECS 201-857-5, MFCD00011688, 25154-55-6, AI3-14893, DSSTox_CID_1790, DSSTox_RID_76328, DSSTox_GSID_21790, AB-131/40228446, Hydroxy(2-Hydroxyphenyl)oxoammonium, CAS-88-75-5, o-nitro-phenol, CG3, 2-nitrophenyl alcohol, o-Nitrophenol [UN1663] [Poison], 2-(dihydroxyamino)phenol, AC1L1NNM, WLN: WNR BQ, AC1Q5AV9, UNII-BD148E95KD, SCHEMBL26026, N19702_ALDRICH, KSC202Q1L, 48548_SUPELCO, BIDD:ER0656, CHEMBL14205, 33444_RIEDEL, 35966_RIEDEL, AC1Q787K, AC1Q791H, ARONIS020854, BD148E95KD, SR-1C4, SCHEMBL11524557, 33444_FLUKA, 35966_FLUKA, CTK1A2815, NSC1552, MolPort-000-690-271, 824-39-5 (hydrochloride salt), NSC-1552, STR00905, Tox21_201442, Tox21_302758, ANW-58978, AR-1K9216, o-Nitrophenol [UN1663] [Poison], SBB060648, STK011520, ZINC34719541, AKOS000118749, CS21724, LS-1885, MCULE-1415513135, NE10695, RP20508, RTC-063802, TRA0025121, UN 1663, NCGC00090898-01, NCGC00090898-02, NCGC00256357-01, NCGC00258993-01, AJ-89970, AK-54011, AN-24154, CJ-18548, H443, KB-25748, OR000856, OR188118, OR248112, OR362207, SC-18124, AB1003530, KB-173157, ST2417134, TC-063802, FT-0613201, N0153, N0219, ST45034568, C01988, N-3590, 82634-EP2298758A1, 82634-EP2298759A1, 82634-EP2298770A1, 82634-EP2305664A1, 82734-EP2295432A1, 82734-EP2298758A1, 82734-EP2298759A1, 82734-EP2298776A1, 82734-EP2305633A1, 82734-EP2305664A1, 3B4-0434, I01-6053, UNII-UV7XKM40LO component IQUPABOKLQSFBK-UHFFFAOYSA-N, InChI=1/C6H5NO3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8, OPO

Removed Synonyms

null, Phenol, Nitro-, 2-nitrophenol, sodium salt, 2-nitrophenol, ammonium salt, C6H5NO3, PYZD 4409, CID6947, UN1663, C1322, C045573, 423148-78-1, 68585-09-1

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