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

HRID 1680659

반응식

HRID 1680659 반응식
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]

참가 물질

7

반응물 5

HCID 112022-Bromopropene2회HCID 25517Ammonium ChlorideHCID 61041Safranal2회HCID 3028194LithiumHCID 86586944Isopropanol carbon dioxide

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매3회

반응 조건

온도
-10 °C

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-7c6bb549f37f4c0c956817f1531d68ab
출처 데이터셋
uspto-grants-1981_06
특허 번호
US04275087

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