2-Methyl-3-butyn-2-ol → 6-Methyl-5-hepten-2-one

HRID 1676154Notes

Reaction equation

HRID 1676154 reaction equation
CC(O)(C#C)C.[CH3:7][C:8]([OH:17])([CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])C#C.[OH-].[K+]>>[CH3:15][C:14]([CH3:16])=[CH:13][CH2:12][CH2:11][C:8](=[O:17])[CH3:7]

Participants

4

Reactant 3

HCID 82582-Methyl-3-butyn-2-olHCID 14797Potassium HydroxideHCID 62842Dehydrolinalool

Product 1

HCID 98626-Methyl-5-hepten-2-oneYield 95.2%

Procedure

A 100 ml-four-necked flask equipped with a thermometer, a reflux condenser, and a stirrer was charged with 8.61 g (102) mmol 2-methyl-3-butin-2-ol (MBI) and 15.58 g (102) mmol 3,7-dimethyl-6-octen-1-in-3-ol (DLL) stirred with 750 rpm and heated up to reflux temperature. After 5 min an internal temperature of 93° C. was reached, and 2 ml KOH (41.42% in H2O, 20.53 mmol) were added. The reaction was controlled by GC (samples were taken after 60 min, 155 min and 385 min). The ketones were separated by distillation. Yield acetone 5.7 g, (95.8%), yield 6-methyl-5-hepten-2-on (MH) 12.3 g, (95.2%), not optimized.

Workup

  1. customA 100 ml-four-necked flask equipped with a thermometer, a reflux condenser, and a stirrer
  2. temperatureheated up
  3. temperatureto reflux temperature
  4. customwas controlled by GC (samples were taken after 60 min, 155 min and 385 min)
  5. customThe ketones were separated by distillation

Sources & evidence

ORD record
ord-9dc1becf9feb4dbc944c8003f5f79d05
Source dataset
uspto-grants-2011_08
Patent number
US08003843B2

Reaction notes

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