Hydrochloric Acid → HCID 21242373, compound

HRID 1761775Notes

Reaction equation

HRID 1761775 reaction equation
[O:1]1[C:16]([CH3:18])([CH3:17])[CH:2]1[CH2:3][CH2:4]/[C:5](/[CH3:15])=[CH:6]/[CH2:7][CH2:8]/[C:9](/[CH3:14])=[CH:10]/[C:11]([NH2:13])=[O:12].CC([O-])C.CC([O-])C.CC([O-])C.[Al+3].Cl>C1(C)C=CC=CC=1>[OH:1][CH:2]([C:16]([CH3:18])=[CH2:17])[CH2:3][CH2:4]/[C:5](/[CH3:15])=[CH:6]/[CH2:7][CH2:8]/[C:9](/[CH3:14])=[CH:10]/[C:11]([NH2:13])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11143Aluminum isopropoxideHCID 86743001HCID 86743001, compound

Product 1

HCID 21242373HCID 21242373, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4.8 g of (E,E)-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadienamide in 70 ml of toluene is treated with 4.48 g of aluminum isopropylate, whereupon the mixture is boiled under reflux for 4.5 hours. The cooled reaction mixture is poured into a mixture of 2N hydrochloric acid and ice, whereupon the mixture is extracted with 2×100 ml of ether. The combined organic extracts are washed with water and with saturated sodium bicarbonate solution, dried over sodium sulphate, filtered and evaporated. The residue is chromatographed on 230 g of aluminum oxide (basic, activity III), elution being carried out with hexane-ethyl acetate (20% to 100%) and then with ethyl acetate-methanol (10%). There is obtained (E,E)-10-hydroxy-3,7,11-trimethyl-2,6,11-dodecatrienamide as a yellowish, viscous oil. IR (film): 3335, 3195 (OH and NH2); 1668 (amide C=O). MS (CI with NH3): 252 (M+H)+ ; 251 (M+NH4 -H2O)+.

Workup

  1. temperatureunder reflux for 4.5 hours
  2. customThe cooled reaction mixture
  3. extractionis extracted with 2×100 ml of ether
  4. washThe combined organic extracts are washed with water and with saturated sodium bicarbonate solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is chromatographed on 230 g of aluminum oxide (basic, activity III), elution

Sources & evidence

ORD record
ord-15e7a56fa4914a61be5ad8dbaae49f82
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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