Synthesis of 2-naphthol (naphthalen-2-ol)

Preparation of 2-naphthol

Preparation of 2-naphthol (naphthalen-2-ol)

Preparation of 2-naphthol (naphthalen-2-ol)

To 300 g of powdered sodium hydroxide and 30 ml of distilled water are placed in a large copper or nickel crucible and the mixture heated to 280° C. 100 g finely powdered 2-naphthalenesulfonic acid sodium salt are added as quickly as possible, with constant stirring, avoiding that the temperature does not fall below 260° C. When all 2-naphthalenesulfonic acid sodium salt is added the temperature is raised to 320° C. During the reaction the mass froths and steam is evolved, and when the mass becomes liquid consistency the reaction is complete. The length of time for which the fusion is kept at 310-320° C is about five minutes. The top layer of the melt, which is darker than the lower one and contains the sodium 2-naphtholate, is poured on to a copper plate with upturned edges, and, after cooling, the mass is broken up and dissolved in water. The 2-naphthol is precipitated with concentrated hydrochloric acid. After cooling, the 2-naphthol is filtered off, dried, and purified by distillation in vacuo yielding 50-55 g of final product. 2-Naphthol forms colorless, crystalline solid, which melts at 123° C and boils at 286° C, not soluble in water but soluble in many organic solvents.

The Synthetic Dyestuffs and the Intermediate Products from which They are Derived, by J. C. Cain, 213, 1905

IUPAC Name

naphthalen-2-ol

InChI

InChI=1S/C10H8O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11H

InChI Key

JWAZRIHNYRIHIV-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C2C=C(C=CC2=C1)O

MeSH Synonyms

2-hydroxynaphthalene, 2-naphthol, 2-naphthol, (1+), 2-naphthol, 1,4,5,8-(14)C4-labeled, 2-naphthol, 7-(14)C-labeled, 2-naphthol, 8-(14)C-labeled, 2-naphthol, bismuth salt, 2-naphthol, magnesium salt, 2-naphthol, potassium salt, 2-naphthol, sodium salt, 2-naphthol, titanium(4+) salt, beta-naphthol

Depositor-Supplied Synonyms

2-NAPHTHOL, naphthalen-2-ol, 2-Naphthalenol, beta-naphthol, 135-19-3, 2-Hydroxynaphthalene, Betanaphthol, Isonaphthol, Naphthol B, Developer BN, Azogen developer A, Developer A, Developer AMS, 2-Naftolo, 2-Naphtol, 2-Naftol, C.I. Developer 5, beta-Hydroxynaphthalene, beta-Naphtol, beta-Napthol, Developer sodium, .beta.-Naphthol, beta-Monoxynaphthalene, beta-Naphthyl alcohol, beta-Naphthyl hydroxide, NAPHTHOL, BETA, beta-Naftol, beta-Naftolo, Antioxygene BN, C.I. Azoic Coupling Component 1, 2-Napththol, .beta.-Naftolo, .beta.-Naphtol, .beta.-Napthol, .beta.-Naftol, 2-Naftol [Dutch], beta-Naftol [Dutch], 2-Naphtol [French], Caswell No. 590, 2-Naftolo [Italian], beta-Naphtol [German], beta-Naftolo [Italian], .beta.-Naphthyl alcohol, C.I. 37500, .beta.-Monoxynaphthalene, NSC 2044, .beta.-Hydroxynaphthalene, .beta.-Naphthyl hydroxide, UNII-P2Z71CIK5H, CHEMBL14126, CHEBI:10432, HSDB 6812, JWAZRIHNYRIHIV-UHFFFAOYSA-N, EINECS 205-182-7, EINECS 215-322-9, EPA Pesticide Chemical Code 010301, BRN 1817321, AI3-00081, DSSTox_CID_7061, DSSTox_RID_78296, DSSTox_GSID_27061, AB-131/40299865, CAS-135-19-3, Hydronaphthol, napthalen-2-ol, naphth-2-ol, Naphthol, .beta., 03V, 2-hydroxy naphthalene, beta.-hydroxynaphthalene, Microcidin (Salt/Mix), ACMC-1CUIO, AC1L1RGD, 2-oC>>uYA, P2Z71CIK5H, SCHEMBL28781, WLN: L66J CQ, KSC174M7N, 130109_ALDRICH, 185507_ALDRICH, AC1Q78Z7, C10H8O, SGCUT00131, 70448_FLUKA, 70450_FLUKA, CTK0H4676, HMDB12322, NSC2044, 4b32, MolPort-000-872-059, Sodium 2-naphthoxide (Salt/Mix), HMS3264N15, Pharmakon1600-01504501, 875-83-2 (hydrochloride salt), NSC-2044, to_000010, 36294-21-0 (potassium salt), Tox21_201884, Tox21_303038, ANW-75298, NSC758883, SBB040896, STL281866, ZINC00967928, AKOS000119842, AM86551, CCG-213932, MCULE-2675031485, MP-2123, NSC-758883, RTR-002452, NCGC00249132-01, NCGC00257077-01, NCGC00259433-01, AC-10464, AJ-24565, AK109022, AN-23098, BC676809, I980, KB-69406, LS-95400, LS-95402, SC-18950, ZB015511, AB1001922, ST2413621, FT-0613121, N0027, ST50214496, C11713, 4-06-00-04208 (Beilstein Handbook Reference), A806896, 3B4-0494, I14-6807, InChI=1/C10H8O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11, 860440-31-9

Removed Synonyms

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