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Offline SpinzTronics

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synthesis of sulcatol question
« on: June 14, 2014, 02:02:49 AM »
Hi!

I am doing a lab to synthesize sulcatol and I would like to confirm the balanced equations and products formed for the two chemical reactions done in the lab. I would greatly appreciate your help.

Chemical reactions:
1) 6-methyl-5-hepten-2-one and sodium borohydride (NaBH4) in a methanol solvent to produce a primary alcohol (hopefully sucatol)

I have to assume a 3:1 ratio of ketone to NaBH4, so this is what I am thinking of:

                                                                  CH30H
3 mol 6-methyl-5-hepten-2-one  + 1 mol NaBH4 -------> 2 mol HB(-)0(-C)CCC=C(-C)C   Na(+)

The last compound should be a Boron ion, attached to three groups of the ketone alkoxide (at the oxygen) and an H as well. The sodium components is also there too, by the negative of Boron. I was wondering if this is correct assuming the ratio required by the manual. Furthermore, is the methanol used as a solvent to provide the borohydride with stabilizing hydrogen atoms?

2) do a workup by adding water:

2 mol HB(-)0(-C)CCC=C(-C)C   Na(+)  + 3 mol H2O ----> 3 mol CC(-OH)[-H]CCC=C(-C)C  + B(-)(-OH)3(-H)  Na(+)

The primary alcohol, or crude sulcatol is formed in this step ( an OH, H, substituting the double bond Oxygen in the ketone) and the borohydride still needs to be stabilized (Bion with three OH's and an H attached).

3) 1 mol HCl  +  (all of the previous product) ---->  B-(OH)3 + H20 + NaCl (from washing to remove excess water)

the lab says to add enough HCl until the solution has a pH of 2 so the acid neutralizes the base? making it less reactive?

After doing all these reactions, then extracting the compound ( using diethyl ether) is necessary, so my last question is... how does the ether enable saving the sulcatol product by forming the top layer of the extraction o? The ether will dissolve polar and nonpolar organic solvents so the sulcatol isn't dissolved but I am looking for a physical explanation to this, for example, does it attach in some way? Sorry for some of my ignorance, I am trying to know more than required. I hope the SMILES formatting works!

Thank you for taking the time to read this message and thank in advance for your *delete me*

Offline Borek

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Re: synthesis of sulcatol question
« Reply #1 on: June 14, 2014, 03:04:43 AM »
I hope the SMILES formatting works!

Unfortunately, it didn't.
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Offline Dan

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Re: synthesis of sulcatol question
« Reply #2 on: June 14, 2014, 06:22:31 AM »
Use the preview button to proof read before posing. Take care with your formatting - CH3OH, not CH30H.

Sulcatol is a secondary alcohol.
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Offline zsinger

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Re: synthesis of sulcatol question
« Reply #3 on: June 14, 2014, 10:22:57 AM »
FAR shorter and easier methods to your product, provided you have access to necessary reagents.  See Grignard reaction, etc.
           -Zack
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Offline SpinzTronics

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Re: synthesis of sulcatol question
« Reply #4 on: June 15, 2014, 04:34:16 AM »
Thanks everyone, I'll preview the formatting next time. I think I got it now, and you are right zsinger I also found simpler methods to obtain sulcatol. Thanks again!

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