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Synthesis of Geraniol


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Alright, please bear with me as I attempt to detail my proposed method of synthesizing geraniol (3,7-dimethylocta-2Z,6-dien-1-ol). Keep in mind that this is my first multistep synthesis, and with only one semester of organic.

 

First, react ethene with bromine in carbon tetrachloride, yielding 1,2-dibromoethane.

 

Second, react 1,2-dibromoethane with an acetylide anion, yielding 4-bromobut-1-yne. **Now this is where I have my first question...as the first molecules of the product form, would the unreacted acetylide ions displace the other bromine on the 4-bromobut-1-yne.**

 

Let's assume that if we use a stoiciometric ratio of reactants:

 

Third, hydrogenate the alkyne using the P-2 catalyst. This yields 4-bromobut-1-ene. **Second question, if 1 mol of hydrogen was used, would the resulting alkene react with the hydrogen that has yet to react**

 

Assuming that it doesnt...:

 

Fourth, conduct a hydroboration/oxidation on the 4-bromobut-1-ene, yielding 4-bromobutan-1-ol.

 

Oxidize the bromoalcohol with pyridinium chlorochromate, yielding bromobutanal

 

react the bromobutanal with sodium methoxide, yielding but-4-enal.

 

React but-4-enal with Isopropyl magnesium bromide, following up with protonation with ammonium bromide. This yields 2-methylhex-5-en-2-ol.

 

React the alkenol with Hydrogen Bromide in the presence of peroxides, yielding 5-bromo-2-methylhexan-2-ol

 

React 5-bromo-2-methylhexan-2-ol with acetylide ion, yielding 2-methylhept-6-yn-2-ol.

 

Hydrogenate 2-methylhept-6-yn-2-ol using P-2, yielding 2-methylhept-6-en-2-ol

 

React the alkenol with Phosphorus Tribromide yielding 3-bromo-2-methyl-hept-6-ene.

 

Conduct oxymercuration/demercuration, yielding 2-bromo-3-methylhept-6-ol.

 

React alcohol with sodium methoxide, yielding 2-methylhept-2-en-6-ol.

 

Oxidize alcohol with pyridinium chlorochromate, yielding 2-methylhept-2-en-6-one.

 

React ketone with enolate ion of acetaldehyde, yielding geranial.

 

Reduce the aldehyde with Lithium aluminum hydride, yielding the final product, Geraniol.

 

 

Please comment on this, correct any mistakes that I (more than likely) made. I appoligize for the lack of aesthetic appearances.

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