Acetic Acid → trans-4-[2-(Dimethylamino)-ethyl]-4-cyclohexene-1,2-diol

HRID 26267

Reaction equation

HRID 26267 reaction equation
[CH3:1][N:2]([CH3:11])[CH2:3][CH2:4][C:5]1[CH2:10][CH:9]=CC[CH:6]=1.[C:12]([OH:15])(=O)[CH3:13].II.C(OCC)(=[O:20])C>C([O-])(=O)C.[Ag+]>[CH3:1][N:2]([CH3:11])[CH2:3][CH2:4][C:5]1[CH2:10][C@@H:9]([OH:20])[C@H:12]([OH:15])[CH2:13][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 807Iodine2×HCID 8857Ethyl AcetateHCID 122289201-[2-(Dimethylamino)ethyl]-1,4-cyclohexadiene

Product 1

HCID 54092690trans-4-[2-(Dimethylamino)-ethyl]-4-cyclohexene-1,2-diol

Reagents, catalysts & solvents 1

HCID 11246Silver acetateCatalyst

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 isoproanol. 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.

Workup

  1. dissolutiondissolves
  2. temperatureis then heated for two hours at 95°
  3. temperatureThe reaction solution is cooled
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give an oil
  7. washwashed with aqueous sodium bicarbonate solution
  8. dry with materialThe organic phase is dried (MgSO4)
  9. customevaporated to an oil
  10. additiontreated with HCl in isoproanol
  11. customThe resulting crude solid is removed by filtration
  12. customrecrystallized from acetonitrile-ether

Sources & evidence

ORD record
ord-2b7431e995a74a5fb28e43785fa3f5f3
Source dataset
uspto-grants-1979_04
Patent number
US04149001

Linked notes

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