Sodium Hydroxide → 1-Phenylhexan-3-one

HRID 1634638Notes

Reaction equation

HRID 1634638 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>>[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

3

Reactant 2

HCID 14798Sodium HydroxideHCID 10285942215316-49-7

Product 1

HCID 1225021-Phenylhexan-3-one

Conditions

Temperature
80 °C

Procedure

8.5 g of sodium hydroxide prills (213 mmol) in 100 ml of polyethylene glycol 1000 dimethyl ether (m.p.: 42° C.) were initially introduced at room temperature into a 3-necked flask having a dropping funnel, internal thermometer and stirrer. After 25 g of 3-hydroxy-3-(2′-phenylethyl)hexanoic acid (106 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 80° C. for 10 min and then to 150° C. Thereafter, the pressure was reduced to 2.5 mbar and the mixture was stirred for 2 h at 150° C. and a pressure of 2.5 mbar, 1-phenylhexan-3-one formed by cleavage being collected in a cooled receiver. The 1-phenylhexan-3-one collected in the receiver was obtained, after washing with 20 ml of water, in a yield of 12.1 g (81% of theory) with a boiling point of 133° C. (13 mbar).

Workup

  1. addition63, 7348 (1998), had been added
  2. customto 150° C

Sources & evidence

ORD record
ord-096cb0b7181347c3b0c2a6dce28afa34
Source dataset
uspto-grants-2003_01
Patent number
US06506942B2

Reaction notes

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