HCID 21242373, compound → HCID 21242302, compound

HRID 1761776Notes

Reaction equation

HRID 1761776 reaction equation
[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]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:14]/[C:9](/[CH2:8][CH2:7]/[CH:6]=[C:5](\[CH3:15])/[CH2:4][CH2:3][C:2](=[O:1])[C:16]([CH3:18])=[CH2:17])=[CH:10]\[C:11]([NH2:13])=[O:12]

Participants

4

Reactant 1

HCID 21242373HCID 21242373, compound

Product 1

HCID 21242302HCID 21242302, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.9 g of (E,E)-10-hydroxy-3,7,11-trimethyl-2,6,11-dodecatrienamide in 50 ml of methylene chloride is treated with 19.0 g of manganese dioxide ("precipitated", activated by heating to 110° for 15 minutes) and the resulting suspension is stirred at room temperature for 16 hours. After filtration over Hyflo the filtrate is concentrated and the yellow oil obtained is chromatographed on 100 g of aluminum oxide (neutral, activity III) with hexane-ethyl acetate (50% to 100%). There is obtained (E,E)-3,7,11-trimethyl-10-oxo-2,6,11-dodecatrienamide as a colourless oil which crystallizes upon standing, m.p. 42°-44°. IR (film): 3428, 3347, 3194, (NH2); 1671 (amide C=O, ketone conj. C=O). MS (CI with NH3): 250 (M+H)+.

Workup

  1. filtrationAfter filtration over Hyflo the filtrate
  2. concentrationis concentrated
  3. customthe yellow oil obtained
  4. customis chromatographed on 100 g of aluminum oxide (neutral, activity III) with hexane-ethyl acetate (50% to 100%)

Sources & evidence

ORD record
ord-ec7965bec40f401da66babd4a519a34a
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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