Hydrochloric Acid → 1-Phenylhexan-3-one

HRID 1634637Notes

Reaction equation

HRID 1634637 reaction equation
[OH-].[Na+].[OH:3][C:4]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH2:9][CH2:10][CH3:11])CC(O)=O.Cl>CCCCCCCCC>[C:14]1([CH2:13][CH2:12][C:4](=[O:3])[CH2:9][CH2:10][CH3:11])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10285942215316-49-7

Product 1

HCID 1225021-Phenylhexan-3-one

Reagents, catalysts & solvents 1

HCID 8141NonaneSolvent

Conditions

Temperature
155 °C

Procedure

6.8 g of sodium hydroxide prills (170 mmol) in 100 ml of a nonane fraction (b.p.: 148-153° C.) were initially introduced at room temperature into a three-necked flask having a reflux condenser, internal thermometer and stirrer. After 20 g of 3-hydroxy-3-(2′-phenylethyl)hexanoic acid (85 mmol), prepared according to K. S. Fors, J. R. Gage, R. F. Heier, R. C. Kelly, W. R. Perrault and N. Wicnienski, J. ORG. CHEM. 63, 7348 (1998), had been added, the mixture was heated to 155° C., a clear solution initially forming. The mixture was stirred for 2 h at 150° C., a colorless precipitate forming. The mixture was then allowed to cool to 20° C., hydrolyzed with 80 ml of 2 N hydrochloric acid (pH 1) and stirred for 15 min and the organic phase separated. The organic phase was washed with 30 ml of saturated sodium bicarbonate solution. After phase separation, drying was effected over sodium sulfate and the solvent was distilled off under reduced pressure (>90% of the solvent was recovered). 1-phenylhexan-3-one was obtained in a yield of 13.6 g (91% of theory) with a boiling point of 134° C. (13 mbar).

Workup

  1. addition63, 7348 (1998), had been added
  2. customa clear solution initially forming
  3. customa colorless precipitate forming
  4. stirringstirred for 15 min
  5. customthe organic phase separated
  6. washThe organic phase was washed with 30 ml of saturated sodium bicarbonate solution
  7. customAfter phase separation
  8. customdrying
  9. distillationthe solvent was distilled off under reduced pressure (>90% of the solvent was recovered)

Sources & evidence

ORD record
ord-803b912370ed43df89a58d91b8809f18
Source dataset
uspto-grants-2003_01
Patent number
US06506942B2

Reaction notes

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