2-溴丙烯 → 2,6,6-TRIMETHYL-alpha-ISOPROPENYL-1,3-CYCLOHEXADIENE-1-METHANOL

HRID 127147

反应方程式

HRID 127147 反应方程式
C(=O)=O.[CH:4](O)([CH3:6])[CH3:5].[Li].BrC(C)=C.[CH3:13][C:14]1[CH:19]=[CH:18][CH2:17][C:16]([CH3:21])([CH3:20])[C:15]=1[CH:22]=[O:23].[Cl-].[NH4+]>C(OCC)C>[CH3:13][C:14]1[CH:19]=[CH:18][CH2:17][C:16]([CH3:20])([CH3:21])[C:15]=1[CH:22]([C:4]([CH3:6])=[CH2:5])[OH:23]

参与物

7

反应物 5

HCID 112022-溴丙烯2 次HCID 25517氯化铵HCID 61041藏红花醛2 次HCID 3028194锂HCID 86586944Isopropanol carbon dioxide

产物 1

HCID 234527792,6,6-TRIMETHYL-alpha-ISOPROPENYL-1,3-CYCLOHEXADIENE-1-METHANOL

试剂、催化剂与溶剂 1

HCID 3283乙醚溶剂3 次

反应条件

温度
-10 °C

实验过程

Into a 500 ml reaction flask equipped with immersion thermometer, mechanical stirrer, 250 ml addition funnel, Friedrich's condenser, dry ice/isopropyl alcohol bath and gas bubbler is placed 1.9 grams (44.7 cm length) (0.28 gram atoms) of Li wire (cut up) and 100 ml anhydrous diethyl ether. The lithium wire/diethyl ether mixture is cooled with stirring to -10° C. 15.7 Grams (0.13 moles) of 2-bromo-1-propene (dissolved in approximately 40 ml anhydrous diethyl ether) is added dropwise from the addition funnel into the reaction mixture while maintaining the temperature thereof between -10° C. and -5° C. Following addition of the 2-bromo-1-propene, the reaction mass is stirred for a period of 30 minutes while maintaining the reaction mass at a temperature of 0° C. and is then stirred for 1.5 hours at room temperature (20° C.). The reaction mass is then chilled to -20° C. and 15.0 grams (0.10 moles) of Safranal is added dropwise while maintaining the reaction mass at from -20° up to -15° C. Following the addition of the Safranal, the reaction mass is stirred at -20° C. for a period of 15 minutes and then at room temperature for a period of 2.5 hours. The reaction mass is monitored on GLC at 30 minutes, 90 minutes and 150 minutes, at which point the reaction mass is poured into 300 ml of saturated ammonium chloride (aqueous). The reaction mixture is then added to 200 ml of anhydrous diethyl ether. The reaction mass is then washed with saturated aqueous sodium chloride, dried and concentrated yielding 18.67 grams of crude product. 1.0 Grams of crude product is set aside for silica gel chromatography. The remaining 17.56 grams is vacuum distilled yielding the following fractions:

后处理

  1. customInto a 500 ml reaction flask
  2. temperaturewhile maintaining the temperature
  3. custombetween -10° C. and -5° C
  4. stirringthe reaction mass is stirred for a period of 30 minutes
  5. temperaturewhile maintaining the reaction mass at a temperature of 0° C.
  6. stirringis then stirred for 1.5 hours at room temperature (20° C.)
  7. temperatureThe reaction mass is then chilled to -20° C.
  8. temperaturewhile maintaining the reaction mass at from -20° up to -15° C
  9. stirringthe reaction mass is stirred at -20° C. for a period of 15 minutes
  10. waitThe reaction mass is monitored on GLC at 30 minutes, 90 minutes and 150 minutes, at which
  11. washThe reaction mass is then washed with saturated aqueous sodium chloride
  12. customdried
  13. concentrationconcentrated

来源与证据

ORD记录
ord-e9ce1313b7644a8f85263d6a97903333
来源数据集
uspto-grants-1981_03
专利号
US04255293

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