Synthesis of guaiacol

Preparation of guaiacol

Alternative Names: 2-Methoxyphenol; O-Methoxyphenol; 2-Hydroxyanisole; Phenol, 2-methoxy-;

Preparation of guaiacol

Preparation of guaiacol

In a three-necked flask equipped with a stirrer, reflux condenser and dropping funnel 11 g of catechol and 25 ml of nitrobenzene are placed. The obtained mixture is heated to 45° C (bath temperature) and in three portions (at intervals of 10 minutes) 16.5 g (or 12.5 ml) of dimethyl sulfate are dropwise added. While vigorously stirring and maintaining the temperature (45° C) 20 ml of a 20% solution of sodium hydroxide are added at such rate that the reaction mixture always remained weakly alkaline (pH 8-9). After the reaction is complete (about 30 min), dilute sulfuric acid is added until the pH is acidic. The organic layer is separated and the aqueous layer is extracted with ether (3 x 10 ml). The organic layer and ether extracts are combined and additionally treated with 2N sodium hydroxide solution (3 x 20 ml) in order to extract guaiacol in the form of sodium salt. The obtained the alkaline solution of guaiacol is carefully separated from the organic layer. In case, of the emulsion formation the alkaline solution of guaiacol can be additionally extracted with 25 ml of ether and the obtained extract is discarded. Very careful separation of the organic layer from the alkaline solution of guaiacol should be achieved as the separation of guaiacol from nitrobenzene is more complicated. I order to obtain guaiacol the alkaline extract is acidified with dilute sulfuric acid and extracted with ether (4 x 20 ml), the ether extracts are combined and dried over calcium chloride. Ether is distilled off and the residue is purified by distillation. Yield about 8 g (65% of theory); b.p. 199-201 ° C at 760 mm Hg; nD=1.5415.

Лабораторные работы в органическом практикуме, А.Е., Агрономов, 64-65, 1974 (Laboratory work in the organic practice, A. E, Agronomov, 64-65, 1974)

IUPAC Name

2-methoxyphenol

InChI

InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3

InChI Key

LHGVFZTZFXWLCP-UHFFFAOYSA-N

Canonical SMILES

COC1=CC=CC=C1O

MeSH Synonyms

2-Hydroxy-Anisole, 2-Hydroxyanisole, 2-Methoxy-Phenol, 2-Methoxyphenol, Catechol, Methyl, Guaiacol, Guaicol, Methyl Catechol

Depositor-Supplied Synonyms

guaiacol, 2-Methoxyphenol, o-Methoxyphenol, 2-Hydroxyanisole, 90-05-1, Phenol, 2-methoxy-, Guaicol, 1-Hydroxy-2-methoxybenzene, Guaicolina, Methylcatechol, Anastil, Guaiastil, Guajol, Guasol, Pyroguaiac acid, Catechol monomethyl ether, o-Guaiacol, o-Hydroxyanisole, Pyrocatechol monomethyl ether, Phenol, o-methoxy-, O-Methyl catechol, 2-Methoxy-Phenol, Methoxyphenol, Guajakol, Methyl Catechol, CREOSOTE, WOOD, Hydroxyanisole, Methylcatachol, Creodon, Guajacol, 2-methoxy phenol, Phenol, methoxy-, Guajakol [Czech], Guaiacol (JAN), Guaiacol (natural), Creodon (TN), NSC 3815, Pyrocatechol methyl ester, UNII-6JKA7MAH9C, CHEMBL13766, FEMA No. 2532, CCRIS 2943, CHEBI:28591, HSDB 4241, LHGVFZTZFXWLCP-UHFFFAOYSA-N, Guaiacol [JAN], EINECS 201-964-7, SBB058681, NCGC00090827-02, NCGC00090827-04, AI3-05615, DSSTox_CID_3113, DSSTox_RID_76880, DSSTox_GSID_23113, 8021-39-4, Creosote, CAS-90-05-1, guiacol, methoxy phenol, ortho-Guaiacol, 6-methoxyphenol, o-Guiacol, o–methoxyphenol, orthomethoxyphenol, o-methoxy-Phenol, 2-methoxyphenol;, ortho-methoxyphenol, JZ3, 2-(methyloxy)phenol, 6JKA7MAH9C, bmse000436, bmse010027, AC1L19AA, WLN: QR BO1, DSSTox_RID_77552, DSSTox_GSID_24853, SCHEMBL21626, ghl.PD_Mitscher_leg0.900, guaiacol (liquid) extra pure, PHENOXY, 2-METHOXY-, KSC204S1J, MLS001055375, G5502_SIGMA, W253200_ALDRICH, AC1Q46B5, 50880_FLUKA, CTK1A4914, HMDB01398, NSC3815, MolPort-000-871-969, HMS2089D18, HMS2233P04, HMS3372N11, Pharmakon1600-01506165, ACMC-209784, NSC-3815, STR03604, Tox21_111031, Tox21_201136, Tox21_202990, Tox21_400004, ANW-13634, BDBM50240369, DNC009129, NSC760376, STL281868, ZINC13512224, AKOS000118831, CCG-214035, EBD2205193, LS-1906, MCULE-5627336368, NSC-760376, PS-3252, RTR-028311, NCGC00090827-01, NCGC00090827-03, NCGC00090827-05, NCGC00090827-06, NCGC00090827-07, NCGC00258688-01, NCGC00260535-01, AJ-63992, AK114448, AN-17339, BT000121, KB-30331, OR025059, OR153692, OR163668, OR268520, OR343147, SC-18105, SMR000059155, CAS-8021-39-4, AB1001888, DB-024854, ST2410094, TR-028311, FT-0626815, M0121, ST50214385, 7519-EP2292227A2, 7519-EP2295426A1, 7519-EP2295427A1, 7519-EP2305636A1, 7519-EP2305683A1, 7519-EP2308857A1, 7519-EP2308861A1, 7519-EP2311821A1, 7519-EP2311839A1, 7519-EP2314584A1, 7519-EP2314589A1, 7519-EP2316470A2, 7519-EP2316832A1, 7519-EP2316833A1, 7519-EP2316837A1, C01502, C15572, D00117, AB00876226-06, 196981-EP2269977A2, 196981-EP2371803A1, 196981-EP2377843A1, A843426, I01-6054, 3B3-032623, InChI=1/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H, 2-Methoxyphenol, Catechol monomethyl ether, Pyrocatechol monomethyl ether, 2-Methoxyphenol; Catechol monomethyl ether; Pyrocatechol monomethyl ether, 26638-03-9

Removed Synonyms

Propenylguaiacol, Catechol, Methyl, Beechwood creosote, 4-Propenylguaiacol, 2-Hydroxy-Anisole, Creosote, beechwood, 2-Methoxy-4-propenylphenol, C7H8O2, CID460, D003407, D006139, ACN-035755 1990-5-1

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