Synthesis of 2-allylphenol (o-chavicol)

Preparation of 2-allylphenol

Preparation of 2-allylphenol (o-Chavicol)

Preparation of 2-allylphenol (o-Chavicol)

Allyl phenyl ether is boiled under an air condenser until the temperature no longer rises, a process requiring four to six hours. From an initial temperature of about 190° C the thermometer finally rises to about 220° C. After the boiling has been completed the product is cooled, dissolved in 20 % aqueous sodium hydroxide, and the solution is extracted with petroleum ether to remove traces of unchanged allyl phenyl ether. The 2-allylphenol is then treated with sulfuric acid, and crude 2-allylphenol extracted with ether, dried over sodium sulfate, and ether is evaporated. Distillation of crude 2-allylphenol in vacuum yields an oil, boiling at 109-100° C under a pressure of 22 mm and solidifying in a freezing mixture to a mass of crystals which melt at —6°. The yield is almost quantitative.

An advanced laboratory manual of organic chemistry, M. Heidelberger, 37-39, 1923

IUPAC Name

2-prop-2-enylphenol

InChI

InChI=1S/C9H10O/c1-2-5-8-6-3-4-7-9(8)10/h2-4,6-7,10H,1,5H2

InChI Key

QIRNGVVZBINFMX-UHFFFAOYSA-N

Canonical SMILES

C=CCC1=CC=CC=C1O

MeSH Synonyms

2-allylphenol, 2-allylphenol potassium, 2-allylphenol sodium

Depositor-Supplied Synonyms

2-ALLYLPHENOL, o-Allylphenol, 1745-81-9, Phenol, o-allyl-, Phenol, 2-(2-propenyl)-, 2-allyl-phenol, 2-(prop-2-en-1-yl)phenol, 2-prop-2-enylphenol, 2-(2-Propenyl)phenol, 2-prop-2-en-1-ylphenol, CHEBI:39826, Phenol, 2-(2-propen-1-yl)-, QIRNGVVZBINFMX-UHFFFAOYSA-N, NSC 1538, EINECS 217-119-0, BRN 0742121, AI3-17107, 2LP, Allyl Phenol, 2-allyl phenol, (2-Propenyl)phenol, ZINC01576883, 2-Allyl Phenol WP, (prop-2-enyl)phenol, ACMC-1BRVQ, 2-(2-Propenyl)-phenol, Phenol, (2-propenyl)-, DSSTox_CID_2164, AC1L26AC, AC1Q78AO, 3-(2-hydroxyphenyl)propene, DSSTox_RID_76510, UNII-O04F145ZJZ, DSSTox_GSID_22164, WLN: QR B2U1, A34805_ALDRICH, SCHEMBL160157, O04F145ZJZ, CHEMBL1229950, 3383-08-2 (hydrochloride), NSC1538, MolPort-001-766-686, BB_SC-1155, 1-ALLYL,2-HYDROXY-BENZENE, NSC-1538, Tox21_302056, ANW-22717, BBL027374, SBB044905, STK802467, AKOS000274969, DB02534, MCULE-3496703080, RP20146, NCGC00255154-01, AN-20711, CJ-24972, KB-67990, SC-65386, CAS-1745-81-9, LS-103844, RT-003614, A0233, FT-0610996, ST50817962, V1499, 4-06-00-03807 (Beilstein Handbook Reference), I01-3761, 3B3-032656, InChI=1/C9H10O/c1-2-5-8-6-3-4-7-9(8)10/h2-4,6-7,10H,1,5H, 26761-75-1

Removed Synonyms

o-Allyl phenol, 2-allylphenol sodium, 2-allylphenol potassium, Phenol, 2-(propenyl)-, CID15624, C099328

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