Author Topic: Ethyl Chloride  (Read 1562 times)

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amalgum

  • Guest
Re: Ethyl Chloride
« Reply #20 on: January 04, 2002, 06:04:00 AM »
How about this:
EtOH + NaCl + H2SO4 ----> EtCl + Na2SO4 + H20
(I think I may have that slightly screwed up, but I know it works)

timsong

  • Guest
Re: Ethyl Chloride
« Reply #21 on: January 04, 2002, 02:18:00 PM »
I've read about sulphuric acid being used in the prep of alkyl bromides by treating the alcohol with a mixture of aqueous sodium bromide and sulphuric acid.
But as far as ethyl chloride is concerned I have only read about it being prepared with hydrochloric acid and zinc chloride or via a halogen hydride, phosphorus halide or thionyl chloride.


amalgum

  • Guest
Re: Ethyl Chloride
« Reply #22 on: January 04, 2002, 07:20:00 PM »
Well HCl acid and Zn can still be done easily. The materials are easy to get. SWIM could do it right now without even leaving the house.

Peaktime

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Zinc Chloride
« Reply #23 on: February 03, 2003, 12:16:00 AM »

YourMomma7111

  • Guest
CH3CH2Cl --> CH3CH2NH2 --> CH3CH2NO2
« Reply #24 on: February 04, 2003, 12:28:00 AM »
EtCl refluxed in excess ammonia leads to ethylamine via an Sn2 reaction.  Sn2 reactions are one-step, proceed best at primary carbons (such as is the case with EtCl) and require the use of an aprotic solvent such as dimethylformamide (DMF), acetonitrile (CH3CN), or dimethylsulfoxide (CH3SOCH3).  The former three solvents do not have any acidic hydrogens which can solvate anions, although they can still solvate cations such as K+.  Since ammonia (NH3) is the nucleophile in this reaction, this means that these solvents will not hinder its nucleophilicity nearly as much as would a protic solvent, such as AcOH would, due to the lack of intermolecular hydrogen bonding.

Ethylamine is useful in and of itself in the synthesis of EVE (mdea), but it can also be oxidized to nitroethane via a peracid.  A peracid is of the form R-CO-O-OH.  For example, mixing 30% hydrogen peroxide (H2O2) and glacial ("pure") acetic acid (CH3CO2H) yields CH3CO-O-OH.  Peracids are extremely oxidizing due to their intrinsic instability. 

Nitroethane is very useful in turning benzaldehyde or substituted benzaldehydes (such as vanillin or pyridoxine or nicotinic aldehyde) into amphetamines if an ammonium catalyst source is used in the first step (such as cyclohexylamine or ammonium acetate) followed by reduction with LiAlH4 (LAH) in dry ether (such as THF or diethyl ether) followed by dropwise acid hydrolysis with IPA (isopropyl alcohol) or simply water.  After acid/base extractions and fractional distillation, the freebase amphetamine is easily crystallized by bubbling HCl gas through a solution of the oily freebase in dry ether.

So yes, ethyl chloride is quite useful.  It can be made by reacting ethane with Cl2 gas under ultraviolet light (hv) via a free radical mechanism.