solo
International Hazard
Posts: 3967
Registered: 9-12-2002
Location: Estados Unidos de La Republica Mexicana
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Mood: ....getting old and drowning in a sea of knowledge
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3-phenylpropan-1-ol chlorination
After looking through the google findings I'm not able to conclude any method to chlorinate C6H5-CH2-CH2-CH2-OH (3-phenylpropan-1-ol) I've thought of
using thionly chloride, however not sure of what the conditions are and solvent to use and the after extraction of the chlorinated compound.
Any assistance to resolve this is appreciated, as I have a cousin of this compound needing the same cure................I have a gut feeling that a
chlorinated solvent should be used i.e. chloroform or DCM, but the the isolation of the produced compound, not sure, might precipitate out with
acetone or the hard to find ethyl ether .......I know "experiment is king"....I just want to avoid waste of material .......solo
It's better to die on your feet, than live on your knees....Emiliano Zapata.
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Isomeric_Fred
Harmless
Posts: 31
Registered: 25-6-2006
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Mood: curious
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i havent looked solo, but cyanuric chloride might be good for your needs. AFAIK it is excellent in chlorinating alcohols.
Thionyl chloride is a nasty bugger, and if you look at orgsyn u will find several refs using it on alcohols of various structures. usually a 4-10mol
eq of thionyl chloride is used, and it is advisable to use a vapor trap with NaOH or other suitable compound to catch and render the SO2 gas that will
be given off non toxic.
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Sandmeyer
National Hazard
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Registered: 9-1-2005
Location: Internet
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Mood: abbastanza bene
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You can use neat SOCl2, just remove it at the pump after the rxn and you will have the chloride.
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