Sodium Hydroxide → 3-(Cyclohexylmethylidene)-5-methyloxolan-2-one

HRID 36777

Reaction equation

HRID 36777 reaction equation
[C:1]([CH:4]1[CH2:8][CH:7]([CH3:9])[O:6][C:5]1=[O:10])(=O)[CH3:2].[OH-].[Na+].[CH:13]1(C=O)[CH2:18][CH2:17]C[CH2:15][CH2:14]1>C(OC(OCC)CC)C>[CH:2]1([CH:1]=[C:4]2[CH2:8][CH:7]([CH3:9])[O:6][C:5]2=[O:10])[CH2:17][CH2:18][CH2:13][CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 16275CyclohexanecarboxaldehydeHCID 978463-Acetyl-5-methyloxolan-2-one

Product 1

HCID 538805733-(Cyclohexylmethylidene)-5-methyloxolan-2-oneYield 97.8%

Reagents, catalysts & solvents 1

HCID 20858Propane, 1,1-diethoxy-Solvent2×

Procedure

Example I was repeated using propionaldehyde diethyl acetal as the azeotroping solvent for the reaction. For the reaction 100 ml propionaldehyde diethyl acetal was charged to the reactor with 14.9 g (0.10 mole) 3-acetyl-5-methyldihydro-2(3H)-furanone. The mixture was stirred and 4 g (0.10 mole) powdered sodium hydroxide added. The mixture was allowed to stir for 10 minutes and then heated to reflux for 51/2 hours after which time 14.0 g (0.125 mole) cyclohexanecarboxaldehyde was added over a one-hour period. The mixture was heated under reflux for an additional twelve hours, cooled and worked up to recover 19 g crude 3-cyclohexylmethylene-5-methyldihydro-2(3H)-furanone (59% yield). The structure of the product was confirmed by proton and carbon nuclear magnetic resonance spectroscopy.

Workup

  1. customfor the reaction
  2. additionadded
  3. stirringto stir for 10 minutes
  4. temperatureheated
  5. additionwas added over a one-hour period
  6. temperatureThe mixture was heated
  7. temperatureunder reflux for an additional twelve hours
  8. temperaturecooled

Sources & evidence

ORD record
ord-30a4a3242f2646b08954fcbe4f12329c
Source dataset
uspto-grants-1995_05
Patent number
US05416224

Linked notes

Loading…