Synthesis of camphoric acid

Preparation of camphoric acid

Preparation of camphoric acid

Preparation of camphoric acid

Camphorqumone is extremely sensitive to oxidizing agents and yields camphoric acid when merely boiled in alkaline solution in the presence of air. The camphorquinone is boiled during one day with 3-4 molecular equivalents of alcoholic solution potassium hydroxide. The alcohol is then evaporated, and the residue dissolved in distilled water. After filtering, the camphoric acid is precipitated with dilute sulfuric acid and recrystallized from water, melting at 176-178° C and giving [α]20 = + 46° in absolute alcohol (c = 1).

An advanced laboratory manual of organic chemistry, M. Heidelberger, 58, 1923

IUPAC Name

(1R,3S)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid

InChI

InChI=1S/C10H16O4/c1-9(2)6(7(11)12)4-5-10(9,3)8(13)14/h6H,4-5H2,1-3H3,(H,11,12)(H,13,14)/t6-,10+/m1/s1

InChI Key

LSPHULWDVZXLIL-LDWIPMOCSA-N

Canonical SMILES

CC1(C(CCC1(C)C(=O)O)C(=O)O)C

Isomeric SMILES

C[C@]1(CC[C@@H](C1(C)C)C(=O)O)C(=O)O

MeSH Synonyms

camphoric acid 1-methyl ester, camphoric acid 1-methyl ester, sodium salt, camphoric acid 1-methyl ester, sodium salt, (cis)-(+-)-isomer, camphoric acid monomethyl ester, methyl sodium camphorate, monomethyl camphorate, monomethyl camphorate, sodium salt, (cis)-(+-)-isomer

Depositor-Supplied Synonyms

(1R,3S)-(+)-Camphoric acid, (1R,3S)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid, dextrocamphoric acid, 124-83-4, D(+)-Camphoric acid, Camphoric acid, D-(+)-Camphoric acid, d-Camphoric acid, SBB057929, (1R,3S)-camphoric acid, UNII-W77RM1CSD5, (+-)-Camphersaeure, PubChem7925, Camphoric acid [USP], C409_ALDRICH, AC1L2RL2, AC1Q5QH4, W77RM1CSD5, SCHEMBL52395, KSC174Q4H, CTK0H4843, (+)-(1R,3S)-camphoric acid, LSPHULWDVZXLIL-LDWIPMOCSA-N, MolPort-003-927-875, 5394-83-2, EINECS 226-404-9, AR-1I3662, AKOS015960508, NSC 174634, AC-11594, AJ-94606, AK-47796, KB-49602, ST2414093, TR-003801, FT-0693193, 1,2,2-Trimethyl-1,3-cyclopentanedicarboxylic acid, (+-)-1,2,2-Trimethyl-1,3-cyclopentandicarbonsaeure, UNII-32K0C7JGCJ component LSPHULWDVZXLIL-LDWIPMOCSA-N, (1R,3S)-1,2,2-Trimethyl-1,3-cyclopentanedicarboxylic acid, (3S,1R)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid, 1,3-Cyclopentanedicarboxylic acid, 1,2,2-trimethyl-, cis- (9CI), 1,3-Cyclopentanedicarboxylicacid, 1,2,2-trimethyl-, (1R,3S)-

Removed Synonyms

(+)-Camphoric acid, UNII-32K0C7JGCJ, CID101807, CB10498, 17839-62-2, 18228-72-3

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