Reaction #631991

Reaction equation

HCl

δ-damascone

1-dodecanthiol

DBU

→

3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone

Solvents

THF

Conditions

Workup

1. 1
   Extractionextracted twice with ether
2. 2
   Washwashed with H2O, saturated aqueous NaHCO3
3. 3
   Dryingbrine, dried over Na2SO4
4. 4
   Concentrationconcentrated at 70° C./0.01 mbar

Procedure

A solution of δ-damascone (10.0 g; 52.1 mmol) and 1-dodecanthiol (8.42 g, 41.7 mmol) in THF (150 ml) was treated with DBU (7.92 g; 52.1 mmol) and stirred at 45° C. for 90 min. The reaction solution was treated with 5% aqueous HCl, extracted twice with ether, washed with H2O, saturated aqueous NaHCO3, then brine, dried over Na2SO4, and concentrated at 70° C./0.01 mbar. Yield of crude product: 16.2 g (99%).

Source