Synthesis of diacetone alcohol

Preparation of diacetone alcohol (4-hydroxy-4-methylpentan-2-one; diacetonalkohol; diketone alcohol)

Preparation of diacetone alcohol (4-hydroxy-4-methylpentan-2-one; diacetonalkohol; diketone alcohol)

Preparation of diacetone alcohol (4-hydroxy-4-methylpentan-2-one; diacetonalkohol; diketone alcohol)

A 1-liter round-bottomed flask is fitted with a large Soxhlet extractor attached with an efficient reflux condenser. 750 ml (595 g) of acetone, dried over anhydrous potassium carbonate, and a few fragments of porous porcelain are placed in the flask. A two large paper thimbles are placed in the Soxhlet apparatus, one above the other, each filled about three-quarters full with barium hydroxide and the remainder space is filled with glass wool. The flask is heated so that the acetone refluxes back into the extractor rather rapidly and the heating is continued (72-120 hours) until the acetone no longer refluxes. The refluxing may be interrupted without influencing the preparation. When the reaction is complete the excess of acetone is removed by evaporation. The flask is fitted with a fractionating column attached to an efficient condenser set for downward distillation and the residue is distilled under diminished pressure (diacetone alcohol partially decomposes when distilled under normal pressure) collecting fraction boiling at 71-74°/23 mm (or 62-64°/13 mm). The yield is 450 g.

A text book of practical organic chemistry, by A. I. Vogel, 352, 1974

IUPAC Name

4-hydroxy-4-methylpentan-2-one

InChI

InChI=1S/C6H12O2/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3

InChI Key

SWXVUIWOUIDPGS-UHFFFAOYSA-N

Canonical SMILES

CC(=O)CC(C)(C)O

MeSH Synonyms

4-hydroxy-4-methyl-2-pentanone, diacetone alcohol

Depositor-Supplied Synonyms

Diacetone alcohol, 4-HYDROXY-4-METHYL-2-PENTANONE, 4-Hydroxy-4-methylpentan-2-one, 123-42-2, Diacetonalkohol, Diketone alcohol, Diacetonalcohol, Acetonyldimethylcarbinol, 2-Methyl-2-pentanol-4-one, Tyranton, Diacetone-alcool, 2-Pentanone, 4-hydroxy-4-methyl-, Pyranton A, 4-Hydroxy-2-keto-4-methylpentane, Diacetonalcool, Diacetone, Pyranton, Diacetonyl alcohol, 4-Idrossi-4-metil-pentan-2-one, Diacetonealcool, Dimethyl acetonyl carbinol, 4-Hydroxy-4-methylpentanone-2, Caswell No. 280, 2-Hydroxy-2-methyl-4-pentanone, Diacetonalcohol [Dutch], Diacetonalcool [Italian], Diacetonalkohol [German], NSC 9005, Diacetone-alcool [French], CCRIS 6177, CHEBI:55381, HSDB 1152, 4-Hydroxy-4-methyl-pentan-2-on, SWXVUIWOUIDPGS-UHFFFAOYSA-N, 4-Hydroxy-4-methyl pentan-2-one, EINECS 204-626-7, UN1148, EPA Pesticide Chemical Code 033901, BRN 1740440, AI3-00045, 4-Idrossi-4-metil-pentan-2-one [Italian], DSSTox_CID_4917, DSSTox_RID_77580, 4-Hydroxy-4-methyl-pentan-2-on [German, Dutch], DSSTox_GSID_24917, CAS-123-42-2, Pyraton, ACMC-1BVXG, UNII-Q7WP157PTD, 4-Hydroxy-4-methylpentanone, 4-Methyl-2-pentanon-4-ol, Q7WP157PTD, SCHEMBL28494, H41544_ALDRICH, KSC176O7D, 24220_RIEDEL, 4-hydroxy4-methyl-2-pentanone, AC1L1L91, AC1Q1K47, Jsp001572, CHEMBL3182048, 31450_FLUKA, 4-Methyl-4-hydroxy-2-pentanone, CTK0H6771, NSC9005, MolPort-001-779-725, 2-pentanone, 4-hydroxy-4-methyl, 4-hydroxy-4-methyl-pentan-2-one, BB_NC-2286, 4-methyl-4-oxidanyl-pentan-2-one, NSC-9005, (CH3)2C(OH)CH2C(O)CH3, Tox21_201266, Tox21_303479, 4474AA, ANW-61448, BBL027463, LMFA12000071, LS-681, SBB009084, STL146354, ZINC01648359, AKOS005721167, MCULE-2623560163, RL01069, RTR-003687, UN 1148, WLN: QX1 & 1 & 1V1, NCGC00249012-01, NCGC00257419-01, NCGC00258818-01, AJ-28761, AK-41308, AN-43481, CJ-05952, CJ-26683, KB-39088, TR-003687, FT-0624587, ST51047025, Diacetone alcohol [UN1148] [Flammable liquid], 171962-EP2281810A1, 4-01-00-04023 (Beilstein Handbook Reference), 4-Hydroxy-4-methyl-pentan-2-on(GERMAN, DUTCH), A805073, Diacetone alcohol [UN1148] [Flammable liquid], 3B4-0202, S14-1442, InChI=1/C6H12O2/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H

Removed Synonyms

CID31256, C080344, MPD

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