Reaction #94678

Reaction equation

iodine

ethyl acetate

1-[2-(dimethylamino)-ethyl]-1,4-cyclohexadiene

iodine

acetic acid

→

trans-4-[2-(dimethylamino)-ethyl]-4-cyclohexene-1,2-diol

Conditions

Workup

1. 1
   workup.DISSOLUTIONdissolves
2. 2
   Temperatureis then heated for two hours at 95°
3. 3
   TemperatureThe reaction solution is cooled
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated in vacuo
6. 6
   Otherto give an oil
7. 7
   Washwashed with aqueous sodium bicarbonate solution
8. 8
   DryingThe organic phase is dried (MgSO4)
9. 9
   Otherevaporated to an oil
10. 10
    workup.ADDITIONtreated with HCl in isopropanol
11. 11
    OtherThe resulting crude solid is removed by filtration
12. 12
    Otherrecrystallized from acetonitrile-ether

Procedure

A solution of 45 g. (0.3 moles) of 1-[2-(dimethylamino)-ethyl]-1,4-cyclohexadiene from Example 3(a) in 1.5 l. of dry glacial acetic acid is treated with 100 g. of silver acetate and 75 g. of iodine. The mixture is stirred until most of the iodine dissolves and is then heated for two hours at 95°. The reaction solution is cooled, filtered and evaporated in vacuo to give an oil. The oil is taken up in ethyl acetate and washed with aqueous sodium bicarbonate solution. The organic phase is dried (MgSO4) and evaporated to an oil. The oil is taken up in ethyl acetate and treated with HCl in isopropanol. The resulting crude solid is removed by filtration and recrystallized from acetonitrile-ether to yield dl-trans-4-[2-(dimethylamino)-ethyl]-4-cyclohexene-1,2-diol, diacetate ester, hydrochloride salt.

Source