Diethyl Ether → alpha-Allyl-alpha,3,3-trimethyl-2-norbornane-methanol

HRID 1112626

반응식

HRID 1112626 반응식
[Mg].[CH2:2](Cl)[CH:3]=C.[C:6]([CH:9]1[C:14]([CH3:16])([CH3:15])[CH:13]2[CH2:17][CH:10]1[CH2:11][CH2:12]2)(=[O:8])[CH3:7].[NH4+].[Cl-].[CH3:20]COCC>>[CH2:7]([C:6]([CH3:20])([CH:9]1[C:14]([CH3:16])([CH3:15])[CH:13]2[CH2:17][CH:10]1[CH2:11][CH2:12]2)[OH:8])[CH:2]=[CH2:3]

참가 물질

6

반응물 5

HCID 3283Diethyl EtherHCID 7850Allyl chloride2회HCID 25517Ammonium ChlorideHCID 1625121-(3,3-Dimethylbicyclo(2.2.1)hept-2-yl)ethane-1-oneHCID 5462224Magnesium

생성물 1

HCID 21319797alpha-Allyl-alpha,3,3-trimethyl-2-norbornane-methanol

실험 절차

The magnesium turnings are placed into a 1 liter, 3 neck reaction flask, followed by 200 cc of anhydrous ether. Approximately 6 cc of allyl chloride is added to initiate formation of the Grignard reagent. When the reaction is initiated, the remaining allyl chloride is added dropwise over a 2 hour period, with moderate reflux. After the addition, reflux is continued for 1 hour; at which time 28.5 g 2-acetyl-3,3-dimethylnorbornane is introduced over a 20 minute period. The reaction is very exothermic during this addition. At the end of the addition, refluxing is continued for 1 hour. The work is carried out by hydrolyzing with NH4Cl solution, filtering and separating the layers. The organic layer is washed with two 200 cc portions of water, dried over MgSO4, filtered and concentrated to give 34 grams of oil which is distilled to give 26 g of product, b.p. 90°-105° C. at 1-2 mm Hg.

후처리

  1. additionAfter the addition
  2. temperaturereflux
  3. additionThe reaction is very exothermic during this addition
  4. additionAt the end of the addition
  5. temperaturerefluxing
  6. waitis continued for 1 hour
  7. filtrationfiltering
  8. customseparating the layers
  9. washThe organic layer is washed with two 200 cc portions of water
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d575ff2cfa534746bf67057f5c4b784f
출처 데이터셋
uspto-grants-1978_10
특허 번호
US04123393

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