Sodium Hydroxide → (E)-1,1-Dimethoxy-6,10-dimethyl-5,9-undecadien-2-one
Reaction equation
[Na].[CH3:2][O:3][CH:4]([O:12][CH3:13])[C:5](=[O:11])[CH2:6][C:7](OC)=O.C(Br)/[CH:15]=[C:16](/[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])\[CH3:17].CC(=CCC/C(=C/CO)/C)C.[OH-].[Na+]>C(O)C.O>[CH3:2][O:3][CH:4]([O:12][CH3:13])[C:5](=[O:11])[CH2:6][CH2:7]/[CH:15]=[C:16](\[CH3:17])/[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
In 350 ml of anhydrous ethanol was dissolved 17.4 g of sodium metal, and to this was added dropwise 160 g of methyl 4,4-dimethoxyacetoacetate with stirring at room temperature. One hour later, geranyl bromide prepared from 130 g of geraniol was added dropwise to the above-obtained mixture under ice-cooling. The mixture was then allowed to stand overnight at room temperature and refluxed for one hour. To this reaction mixture was added 42 g of sodium hydroxide in a mixture of 1.4 1. of ethanol and 1.18 1. of water, and the mixture was heated under reflux for 6 hours and extracted with n-hexane. The n-hexane extract was distilled under reduced pressure to give 134 g of the desired product, b.p. 92°-95° C./0.05 mmHg.
Workup
- additionwas added dropwise to the above-obtained mixture under ice-
- temperaturecooling
- temperaturerefluxed for one hour
- additionin a mixture of 1.4 1
- temperatureunder reflux for 6 hours
- extractionextracted with n-hexane
- extractionThe n-hexane extract
- distillationwas distilled under reduced pressure
Sources & evidence
- ORD record
- ord-227598ca0b104909abaeec2811c0581d
- Source dataset
- uspto-grants-1981_04
- Patent number
- US04260551
Reaction notes
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