Synthesis of cyclopentanone

Preparation of cyclopentanone (adipic ketone; ketocyclopentane; ketopentamethylene; adipinketon)

Preparation of cyclopentanone (adipic ketone; ketocyclopentane; ketopentamethylene; adipinketon)

Preparation of cyclopentanone (adipic ketone; ketocyclopentane; ketopentamethylene; adipinketon)

A mixture of 200 g of adipic acid and 10 g of finely powdered crystallized barium hydroxide are placed in a 1-liter distilling flask, fitted with a condenser, receiver and thermometer reaching almost the bottom. The mixture is gradually heated to 285-295° C during about 90 minutes and maintained it at this temperature until only a small amount of dry residue remains in the flask. The decarboxylation takes about 2 hours. During the reaction the temperature must not be allowed to rise above 300° C, since at this temperature the adipic acid distils quite rapidly. The cyclopentanone distils slowly accompanied by a little adipic acid and is separated from the water in the distillate, dried with anhydrous potassium carbonate (potassium carbonate also removes the traces of adipic acid). The obtained crude cyclopentanone is purified by distillation collecting fraction boiling at 128-131° C. The yield is 92 g.

A text book of practical organic chemistry, by A. I. Vogel, 340-341, 1974

IUPAC Name

cyclopentanone

InChI

InChI=1S/C5H8O/c6-5-3-1-2-4-5/h1-4H2

InChI Key

BGTOWKSIORTVQH-UHFFFAOYSA-N

Canonical SMILES

C1CCC(=O)C1

MeSH Synonyms

cyclopentanone

Depositor-Supplied Synonyms

CYCLOPENTANONE, Adipic ketone, 120-92-3, Ketocyclopentane, Ketopentamethylene, Adipinketon, Dumasin, cyclopentan-1-one, cyclopentanon, NSC 4122, cyclopentyloxy, CHEMBL18620, UNII-220W81TN3S, CHEBI:16486, HSDB 2822, BGTOWKSIORTVQH-UHFFFAOYSA-N, EINECS 204-435-9, SBB040835, UN2245, AI3-16609, DSSTox_CID_9154, DSSTox_RID_78687, DSSTox_GSID_29154, CAS-120-92-3, oxocyclopentane, cyclo-pentanone, ZINC00895304, WLN: L5VTJ, ACMC-209a8l, AC1L1R0Y, AC1Q6EM8, KSC175E5F, W391018_ALDRICH, 08299_FLUKA, 29770_FLUKA, CTK0H5252, NSC4122, C112402_SIAL, MolPort-000-871-991, 220W81TN3S, NSC-4122, STR00465, Tox21_200244, Tox21_303562, ANW-17539, BBL027340, BDBM50028830, AKOS000118935, MCULE-9455227735, RP18421, RTR-034475, TRA0014375, UN 2245, NCGC00248575-01, NCGC00257495-01, NCGC00257798-01, AN-22836, BP-12623, KB-49297, LS-58062, ZB015018, DB-061830, TR-034475, FT-0624259, ST50214416, Cyclopentanone [UN2245] [Flammable liquid], C00557, Cyclopentanone [UN2245] [Flammable liquid], 22787-EP2272517A1, 22787-EP2272817A1, 22787-EP2272822A1, 22787-EP2272832A1, 22787-EP2275398A1, 22787-EP2280009A1, 22787-EP2280010A2, 22787-EP2281817A1, 22787-EP2289895A1, 22787-EP2292592A1, 22787-EP2292597A1, 22787-EP2292606A1, 22787-EP2292611A1, 22787-EP2295414A1, 22787-EP2295422A2, 22787-EP2295436A1, 22787-EP2298731A1, 22787-EP2298746A1, 22787-EP2298750A1, 22787-EP2298767A1, 22787-EP2298778A1, 22787-EP2305250A1, 22787-EP2305633A1, 22787-EP2305651A1, 22787-EP2308854A1, 22787-EP2311810A1, 22787-EP2314575A1, 22787-EP2314583A1, 22787-EP2314587A1, 22787-EP2315502A1, 28328-EP2269986A1, 28328-EP2272817A1, 28328-EP2272825A2, 28328-EP2272832A1, 28328-EP2275411A2, 28328-EP2277848A1, 28328-EP2277878A1, 28328-EP2287159A1, 28328-EP2292593A2, 28328-EP2295411A1, 28328-EP2298767A1, 28328-EP2301928A1, 28328-EP2305648A1, 28328-EP2305649A1, 28328-EP2305661A1, 28328-EP2305668A1, 28328-EP2308851A1, 28328-EP2314577A1, 117278-EP2281817A1, 117278-EP2298762A2, A804615, 3B4-1255, S14-1450, T7106882, InChI=1/C5H8O/c6-5-3-1-2-4-5/h1-4H

Removed Synonyms

CID8452, c0510, C007201, CP

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