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

HRID 544809Notes

Reaction equation

[CH3:1]/[CH:2]=[CH:3]/[C:4]([CH:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH:9]=[CH:8][CH:7]1[CH3:14])=[O:5].[CH2:15]([SH:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C1CCN2C(=NCCC2)CC1.Cl>C1COCC1>[CH2:15]([S:27][CH:2]([CH3:1])[CH2:3][C:4]([CH:6]1[C:11]([CH3:12])([CH3:13])[CH2:10][CH:9]=[CH:8][CH:7]1[CH3:14])=[O:5])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

Conditions

Temperature: 45 °C

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%).

Workup

extractionextracted twice with ether
washwashed with H2O, saturated aqueous NaHCO3
dry with materialbrine, dried over Na2SO4
concentrationconcentrated at 70° C./0.01 mbar

Sources & evidence

ORD record: ord-7f2cabe36b3a408eb9719295080cf49f
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935669B2

Reaction notes

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