Synthesis of methyl salicylate

Preparation of methyl salicylate (wintergreen oil; salicylic acid methyl ester; methyl 2-hydroxybenzoate)

Preparation of methyl salicylate (wintergreen oil; salicylic acid methyl ester; methyl 2-hydroxybenzoate)

Preparation of methyl salicylate (wintergreen oil; salicylic acid methyl ester; methyl 2-hydroxybenzoate)

In a 500 ml round-bottomed flask, a mixture of 30.4 g. of salicylic acid (0.2 mole), 70 ml of methyl alcohol, and 7 ml of concentrated sulfuric acid are is placed. A boiling chip is added, a reflux condenser is attached, and the mixture is boiled gently on the steam bath for 5-7 hours. The condenser is arranged for downward distillation and the excess alcohol is distilled as long as it comes over easily (the residue should be about one-third to one-half the original volume). The flask is then cooled well under the tap and the residue is poured into a separatory funnel and treated with 70 ml of ether, using a part of this to rinse the flask. The ethereal solution is then washed thoroughly with two 50 ml portions of water in order to remove most of the unreacted alcohol and the sulfuric acid. The mixture is then shaken with 50 ml of 10% sodium bicarbonate solution in order to remove the last traces of sulfuric acid and to separate the ester from any unreacted salicylic acid. The washing with bicarbonate is repeated until no precipitate of salicylic acid forms on acidification of the aqueous layer. The ethereal solution is then separated carefully, poured into a dry flask, and dried with anhydrous magnesium sulfate for at least one-half hour. The dried solution is filtered into a distilling flask, the vessel being rinsed with a little ether. The ether is removed by distillation and the distillation of the ester itself is carried out over a free flame (no gauze). The boiling point of methyl salicylate is 222° C, so a water-cooled condenser is not only unnecessary but inadvisable, on account of the danger of cracking the condenser. An air condenser tube is employed for the distillation procedure. A small fore-run should be collected separately and the main fraction boiling at 220° C is collected yielding 75-80% of methyl salicylate.

Experiments in Organic Chemistry, L. F. Fieser, 65, 1941

IUPAC Name

methyl 2-hydroxybenzoate

InChI

InChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3

InChI Key

OSWPMRLSEDHDFF-UHFFFAOYSA-N

Canonical SMILES

COC(=O)C1=CC=CC=C1O

MeSH Synonyms

Hewedolor, Linsal, methyl salicylate, methyl salicylate sodium salt, methylsalicylate, Metsal Liniment, Rheumabal

Depositor-Supplied Synonyms

methyl salicylate, Methyl 2-hydroxybenzoate, 119-36-8, Gaultheria oil, Wintergreen oil, Betula oil, OIL OF WINTERGREEN, Teaberry oil, Sweet birch oil, Gaultheriaoel, Wintergruenoel, Analgit, Exagien, Flucarmit, Betula, Spicewood Oil, 2-Hydroxybenzoic acid methyl ester, Betula Lenta, Natural Wintergreen Oil, Methyl o-hydroxybenzoate, 2-(Methoxycarbonyl)phenol, 2-Carbomethoxyphenol, Salicylic acid, methyl ester, Birch oil, sweet, Synthetic Wintergreen Oil, Gaultheria oil, artificial, Wintergreen Oil, synthetic, Benzoic acid, 2-hydroxy-, methyl ester, Panalgesic, Theragesic, Heet, Birch oil, o-Hydroxybenzoic acid, methyl ester, 2-Hydroxybenzoic acid, methyl ester, Salicylic Acid Methyl Ester, Caswell No. 577, BIRCH-ME, Methyl2-Hydroxybenzoate, FEMA Number 2745, NSC 8204, Methyl salicylate (natural), UNII-LAV5U5022Y, Metylester kyseliny salicylove, FEMA No. 2745, CCRIS 6259, CHEBI:31832, HSDB 1935, OSWPMRLSEDHDFF-UHFFFAOYSA-N, 2-Hydroxy-benzoic acid methyl ester, EINECS 204-317-7, methyl hydroxybenzoate, EPA Pesticide Chemical Code 076601, Metylester kyseliny salicylove [Czech], Methylester kyseliny salicylove [Czech], BRN 0971516, NCGC00091106-02, AI3-00090, DSSTox_CID_5659, DSSTox_RID_77872, DSSTox_GSID_25659, 68917-75-9, CAS-119-36-8, Black birch oil, Betula lenta oil, Birch Bark oil, Methylis salicylas, Oils, sweet birch, 1-O-methylsalicylate, Salonpas (Salt/Mix), paragraph sign notCaOI, salicylate methyl ester, paragraph sign notAIUO, Theragesic (Salt/Mix), ACMC-1BSKR, Methyl salicylate (TN), methyl-2-hydroxybenzoate, Enamine_001611, AC1L1HHJ, Methyl salicylate [JAN], WLN: QR BVO1, AC1Q42RT, SCHEMBL5312, Methyl salicylate [JAN:NF], KSC175K7B, BIDD:ER0323, W215481_ALDRICH, W274518_ALDRICH, W311308_ALDRICH, Methylester kyseliny salicylove, FEMA No. 2154, CHEMBL108545, GTPL2431, LAV5U5022Y, M2047_SIAL, M6752_SIAL, Methyl salicylate (JP16/NF), 76631_FLUKA, 84332_FLUKA, CTK0H5570, NSC8204, MolPort-001-783-865, BB_SC-7170, HMS1398J05, HMS2089H12, NSC-8204, 7631-93-8 (hydrochloride salt), Birch sweet oil (Betula lenta L.), Tox21_111081, Tox21_201543, Tox21_300137, ANW-17321, BBL010504, LS-616, SBB053705, STK397388, ZINC00000490, AKOS000118977, MCULE-5398249325, Methyl ester of 2-hydroxy-benzoic acid, NE10156, RP21593, RTR-003257, NCGC00091106-01, NCGC00091106-03, NCGC00091106-04, NCGC00091106-05, NCGC00254104-01, NCGC00259093-01, AC-11584, AJ-07901, AK105942, AN-22802, AN-37948, CJ-00014, H364, KB-53924, KB-54838, LS-98262, TS-02010, DB-012808, TR-003257, FT-0612582, FT-0622968, S0015, ST24030969, ST50715363, 1929-EP2272835A1, 1929-EP2272844A1, C12305, D01087, 23256-EP2277848A1, 23256-EP2289892A1, 23256-EP2298735A1, 23256-EP2305250A1, 23256-EP2305688A1, 23256-EP2308867A2, 23256-EP2308870A2, 23256-EP2311824A1, 23256-EP2311842A2, 23256-EP2314584A1, AB01275470-01, AUoC>>u+/-(1/2)(1/4)xEa(1/4)xo yen, 2-oC>>u+/-(1/2)(1/4)xEa(1/4)xo yen, 4-10-00-00143 (Beilstein Handbook Reference), I01-4358, I01-8932, InChI=1/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H, 648434-07-5, 8022-86-4, 90045-28-6

Removed Synonyms

o-Anisic acid, Hewedolor, Rheumabal, Salonpas, Linsal, methylsalicylate, Metsal Liniment, Mixture Name, Benzoic acid, methyl ester, methyl salicylate sodium salt, CID4133, C033069, 8024-54-2

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2 comments

  1. Laura Tew

    Isn’t the ether dangerous? what temp does it distill at and does this interfere with the isolation of the methyl salicylate?

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