Synthesis of 2,5-hexanedione

Preparation of 2,5-hexanedione

Preparation of 2,5-hexanedione

Preparation of 2,5-hexanedione

20 g of diethyl 2,3-diacetylbutanedioate are mechanically shaken for several days with 250 ml (excess) of 5% aqueous sodium hydroxide, and until no diethyl 2,3-diacetylbutanedioate separates on acidification of a sample with dilute hydrochloric acid. The solution is then saturated with potassium carbonate and extracted with ether, the extract is washed with brine to remove alcohol, dried over calcium chloride, and distilled, the fraction 192-198° C being retained. Yield 70%. Colourless liquid; agreeable odour; miscible with water, alcohol and ether; m.p. 9° C; b.p. 194° C; d=0.973 g/ml at 20° C.

Systematic organic chemistry, by W. M. Cumming, 194, 1937.

IUPAC Name

hexane-2,5-dione

InChI

InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3

InChI Key

OJVAMHKKJGICOG-UHFFFAOYSA-N

Canonical SMILES

CC(=O)CCC(=O)C

MeSH Synonyms

2,5-hexanedione, acetone, acetonyl, acetonyl acetone, diacetonyl

Depositor-Supplied Synonyms

Acetonylacetone, 2,5-HEXANEDIONE, Hexane-2,5-dione, 110-13-4, 1,2-Diacetylethane, Acetonyl acetone, Diacetonyl, 2,5-Hexadione, 2,5-Diketohexane, Acetone, acetonyl-, 2,5-Hexandione, alpha,beta-Diacetylethane, NSC 7621, 2,5-Dioxohexane, .alpha.,.beta.-Diacetylethane, CH3COCH2CH2COCH3, UNII-C0Z8884J3P, MLS001065580, CCRIS 2919, OJVAMHKKJGICOG-UHFFFAOYSA-N, EINECS 203-738-3, ACAN, BRN 0506525, SMR000568468, AI3-02399, acetone, acetonyl, acetonylaceton, hexan-2,5-dione, hexan-2,5-dion, 2,5-hexane-di-one, 4-Acetylbutan-2-one, Hexanedione-(2,5), ACMC-1BPT9, cid_8035, DSSTox_CID_10138, DSSTox_RID_78837, DSSTox_GSID_30138, SCHEMBL10001, KSC176K2N, 10890_ALDRICH, 165131_ALDRICH, AC1L1Q46, WLN: 1V2V1, CHEMBL1564795, 00770_FLUKA, 10890_FLUKA, 15972_FLUKA, BDBM73981, CHEBI:85014, CTK0H6526, C6H10O2, NSC7621, MolPort-000-871-964, BB_SC-6911, C0Z8884J3P, ACT02799, NSC-7621, ZINC1683671, Tox21_200618, ANW-16129, BBL027731, LMFA12000081, LS-498, SBB040811, ZINC01683671, AKOS000119007, MCULE-3166810473, RL00428, RP19133, RTR-002120, NCGC00091466-01, NCGC00091466-02, NCGC00258172-01, AN-22586, AT-45693, BC676318, CAS-110-13-4, CJ-06349, CJ-27766, KB-47083, OR019856, OR095694, OR095695, DB-029411, TR-002120, FT-0621812, ST50214379, TL80073737, V2423, K-0675, 4-01-00-03688 (Beilstein Handbook Reference), A802149, I14-4376, Q-200202, 3B3-034179, InChI=1/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H

Removed Synonyms

‘|A’,’|A’-diacetylethane, CID8035, H0101, C011269, HDO

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