beta-Cyclocitral → 2,6,6-TRIMETHYL-alpha-ISOPROPENYL-1-CYCLOHEXENE-1-METHANOL

HRID 1277563

반응식

HRID 1277563 반응식
C(=O)=O.[CH:4](O)([CH3:6])[CH3:5].[Li].[Li].C(OCC)C.BrC(C)=C.[CH3:19][C:20]1[CH2:25][CH2:24][CH2:23][C:22]([CH3:27])([CH3:26])[C:21]=1[CH:28]=[O:29].[Cl-].[NH4+]>C(OCC)C>[CH3:19][C:20]1[CH2:25][CH2:24][CH2:23][C:22]([CH3:26])([CH3:27])[C:21]=1[CH:28]([C:4]([CH3:6])=[CH2:5])[OH:29]

참가 물질

8

반응물 6

HCID 9895beta-Cyclocitral2회HCID 112022-Bromopropene2회HCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 86586944Isopropanol carbon dioxideHCID 131712026Lithium diethyl ether

생성물 1

HCID 234527782,6,6-TRIMETHYL-alpha-ISOPROPENYL-1-CYCLOHEXENE-1-METHANOL

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
20 °C

실험 절차

Into a 500 ml 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 in length) (0.28 gram atoms) of cut up lithium wire and 100 ml anhydrous diethyl ether. The lithium/diethyl ether mixture is cooled to -10° C. 15.7 Grams (0.13 moles) of 2-bromo-1-propene (dissolved in approximately 40 ml anhydrous diethyl ether) is added drop-wise to the reaction mass keeping the temperature at 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 at 0° C. and for a period of 1.5 hours at room temperature (20° C.). The reaction mass is then chilled to -20° C. and 15.2 grams (0.10 moles) of beta cyclocitral (dissolved in approximately 60 ml diethyl ether) is added dropwise while keeping the reaction temperature at between -20° C. ad -15° C. After addition of the beta cyclocitral, the reaction mass is stirred for a period of 15 minutes at -20° C.; and for a period of 120 minutes at +24° C. The reaction mass is then poured into a saturated aqueous ammonium chloride solution, and the resulting organic phase is separated from the aqueous phase. The aqueous phase is washed with anhydrous diethyl ether. The organic phase is washed with saturated brine. The organic phase and the ether extracts are combined and the resulting material is dried and concentrated to yield 19.98 grams of crude material. This material is distilled under vacuum to 5 fractions as follows:

후처리

  1. customat between -10° C. and -5° C
  2. temperatureThe reaction mass is then chilled to -20° C.
  3. customat between -20° C. ad -15° C
  4. stirringthe reaction mass is stirred for a period of 15 minutes at -20° C.
  5. waitand for a period of 120 minutes at +24° C
  6. customthe resulting organic phase is separated from the aqueous phase
  7. washThe aqueous phase is washed with anhydrous diethyl ether
  8. washThe organic phase is washed with saturated brine
  9. customthe resulting material is dried
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c65700aa116f44b183cd76e2e50eef62
출처 데이터셋
uspto-grants-1981_07
특허 번호
US04278098

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