Synthesis of 4-hydroxy-4-methyl-2-pentanone

Preparation of 4-hydroxy-4-methyl-2-pentanone

Preparation of 4-hydroxy-4-methyl-2-pentanone

Preparation of 4-hydroxy-4-methyl-2-pentanone

116 g of pure acetone are cooled to -12° C and treated with a 30% solution of 5 g of potassium cyanide. The mixture is then slowly stirred and 44 g of freshly prepared acetaldehyde dropped in, the temperature being kept below -5° C. The whole is allowed to stand for half an hour in the freezing mixture and 8 hours in an ice chest. 1½ vol of alcohol-free ether are added, and the lower layer of potassium cyanide solution removed. Any remaining potassium cyanide solution is extracted by washing twice with 60 ml of saturated brine, and a third time with 30 ml to ensure a complete extraction. The washing solution is extracted several times with ether and the total ethereal solution dried for 2 hours over anhydrous sodium sulfate (calcium chloride should not be used as it absorbs hydracetylacetone). The ether is removed under reduced pressure and the residue fractionated three times under a pressure of 20 mm, first from 60-110° C, second 70-90° C, and third 77-79° C. Yield of 4-hydroxy-4-methyl-2-pentanone is 25% theoretical. Colourless, viscous liquid, miscible with water or alcohol ; can be salted out of aqueous solution by potassium carbonate; b.p. 760 176-177° C (slight decomposition); b.p. 77-78° C/20mmHg  d=0.978 g/ml at 18° C.

Systematic organic chemistry, by W. M. Cumming, 103-104, 1937.

IUPAC Name

4-hydroxypentan-2-one

InChI

InChI=1S/C5H10O2/c1-4(6)3-5(2)7/h4,6H,3H2,1-2H3

InChI Key

PCYZZYAEGNVNMH-UHFFFAOYSA-N

Canonical SMILES

CC(CC(=O)C)O

Depositor-Supplied Synonyms

4-Hydroxypentan-2-one, 4-HYDROXY-2-PENTANONE, 2-Pentanone, 4-hydroxy-, CH3CH(OH)CH2C(O)CH3, 4161-60-8, NSC263780, AC1L2FKK, 4-Hydroxy-2-pentanone #, SCHEMBL153744, 4-Hydroxy-4-methyl-2-butanone, CTK1D8103, PCYZZYAEGNVNMH-UHFFFAOYSA-N, EINECS 224-003-3, AKOS014026559, NSC-263780, OR035793

Removed Synonyms

CID20112

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