2-(Dimethylamino)ethanol → 3-[2-(Dimethylamino)ethoxy]-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone

HRID 544807Notes

Reaction equation

HRID 544807 reaction equation
[CH3:1]/[CH:2]=[CH:3]/[C:4]([CH:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][CH:8]=[C:7]1[CH3:14])=[O:5].[CH3:15][N:16]([CH2:18][CH2:19][OH:20])[CH3:17].CN(C)C(=N)N(C)C>>[CH3:15][N:16]([CH3:17])[CH2:18][CH2:19][O:20][CH:2]([CH3:1])[CH2:3][C:4]([CH:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][CH:8]=[C:7]1[CH3:14])=[O:5]

Participants

4

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 664601,1,3,3-TetramethylguanidineHCID 5366077(E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one

Product 1

HCID 593040683-[2-(Dimethylamino)ethoxy]-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanoneYield 32%

Procedure

A solution of α-damascone (6.44 g; 33.5 mmol), N,N-dimethylaminoethanol (30.25 ml; 301 mmol) and tetramethylguanidine (TMG) (0.77 g; 6.70 mmol) was heated at 70° C. for 15 h. Afterward, the excess of N,N-dimethylaminoethanol was distilled at ca. 60° C./10 to 2 mbar. The crude product was diluted in diethyl ether (Et2O) and this mixture was extracted with 5% aqueous HCl and washed with water and saturated aqueous NaCl. The combined aqueous phases were basified using aqueous NaOH and extracted twice with ether to recover the crude product in the organic phases. The organic phases were still washed with water and brine, then dried over Na2SO4 and concentrated. Bulb-to-bulb distillation of the crude product (100-125° C./0.05 mbar) afforded 2.94 g of the desired pure product (yield: 32%).

Workup

  1. distillationAfterward, the excess of N,N-dimethylaminoethanol was distilled at ca. 60° C./10 to 2 mbar
  2. additionThe crude product was diluted in diethyl ether (Et2O)
  3. extractionthis mixture was extracted with 5% aqueous HCl
  4. washwashed with water and saturated aqueous NaCl
  5. extractionextracted twice with ether
  6. customto recover the crude product in the organic phases
  7. washThe organic phases were still washed with water and brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. distillationBulb-to-bulb distillation of the crude product (100-125° C./0.05 mbar)

Sources & evidence

ORD record
ord-fef90a884c8b410eaec07245978ae5f9
Source dataset
uspto-grants-2011_05
Patent number
US07935669B2

Reaction notes

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