Reaction equation
[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]Participants
Procedure
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.
Workup
- customReaction
- additionAfter the addition
- temperaturereflux
- additionThe reaction is very exothermic during this addition
- additionAt the end of the addition
- temperaturerefluxing
- waitis continued for 1 hour
- filtrationfiltering
- customseparating the layers
- washThe organic layer is washed with two 200 cc portions of water
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-44556d46bfd84bb8bba596f3fce23ac9
- Source dataset
- uspto-grants-1978_12
- Patent number
- US04130587
Linked notes
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