Synthesis : Glycols(diols) from Alkenes

[jmarjorie]

Dear All,

 

I wish to attain a 'one-pot' synthesis of a diol from an alkene, and have drawn up a reaction scheme; pls let me know if the following is feasible:

Points to note :

1) The Alkene is an aliphatic hydrocarbon and is water soluble

(soluble in Ethanol,the resultant mix is soluble in water)

2) The reaction temperature in all cases is 25 degrees C

3) There are no other functional groups present in the alkene

 

REACTION SEQUENCE

 

C = C + HOCl ---------> C(OH)-C(Cl)

(5% NaOCl, pH 6.5)

 

 

C(OH)-C(Cl) + 2M NaOH (aq) --------> C(OH)-C(OH)

 

 

Is the above scheme feasible and viable ?

If possible, what would be probable yields ?

Will the diol undergo any changes, eg dehydration on heating to 100 deg C

Any side reactions,considering that Ethanol is present with Hypochlorite ?

 

Thanks in advance,

Best regards,

jmarjorie

[Tartaglia]

Ethanol may well oxidise under those conditions to give choral hydrate. Elimination will be discouraged by more water and less ethanol, but will depend on whether there are hydrogens alpha to the chloro group.

Ring closure to form epoxide may occur but they should then hydrolyse fairly easily to give 1,2 diol