Hydrochloric Acid → 1-Butanone, 3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	1-Dodecanethiol	HCID 8195	—
Reactant	1,8-Diazabicyclo(5.4.0)undec-7-ene	HCID 81184	—
Reactant	(2E)-1-(2,6,6-Trimethyl-3-cyclohexen-1-yl)-2-buten-1-one	HCID 5365916	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	1-Butanone, 3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-	HCID 59304072	—

Reaction Conditions

Temperature	45 °C

Reaction Steps

A solution of 8-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%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07723286B2
Source dataset	uspto-grants-2010_05
ORD ID	ord-269368b5c185470db7d2e680240b0c9c
Source note	uspto-grants-2010_05