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

HRID 66131

反応式

HRID 66131 の反応式
[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]

参加物

6

反応物 5

HCID 3283Diethyl EtherHCID 7850Allyl chloride2 回HCID 25517Ammonium ChlorideHCID 1625121-(3,3-Dimethylbicyclo(2.2.1)hept-2-yl)ethane-1-oneHCID 5462224Magnesium

生成物 1

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

実験手順

Reaction: ##STR245## 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 up 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.

後処理

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

出典と根拠

ORDレコード
ord-44556d46bfd84bb8bba596f3fce23ac9
出典データセット
uspto-grants-1978_12
特許番号
US04130587

関連ノート

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