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

HRID 36777

반응식

HRID 36777 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 20858Propane, 1,1-diethoxy-용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-30a4a3242f2646b08954fcbe4f12329c
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05416224

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