Cyclohexanecarboxaldehyde → 3-(Cyclohexylmethylidene)-5-methyloxolan-2-one

HRID 1111320

반응식

HRID 1111320 반응식
[C:1]([CH:4]1[CH2:8][CH:7]([CH3:9])[O:6][C:5]1=[O:10])(=O)[CH3:2].[Na].[CH:12]1(C=O)[CH2:17][CH2:16]C[CH2:14][CH2:13]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])[CH2:16][CH2:17][CH2:12][CH2:13][CH2:14]1

참가 물질

5

반응물 3

HCID 16275CyclohexanecarboxaldehydeHCID 978463-Acetyl-5-methyloxolan-2-oneHCID 5360545Sodium

생성물 1

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

시약·촉매·용매 1

HCID 20858Propane, 1,1-diethoxy-용매

실험 절차

Example I was repeated using propionaldehyde diethyl acetal as the azeotropic solvent for the reaction to produce the -alkylidene lactone. For this experiment 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 hydroxyde 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. additionadded
  2. stirringto stir for 10 minutes
  3. temperatureheated
  4. additionwas added over a one-hour period
  5. temperatureThe mixture was heated
  6. temperatureunder reflux for an additional twelve hours
  7. temperaturecooled

출처 및 근거

ORD 기록
ord-907065d87f554879bd3e0c52d0f88999
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04980342

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