Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2,2-Dilinoleyl-4-(3-hydroxypropyl)-[1,3]-dioxane
Reaction equation
[CH:1]([O:3][CH:4]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33]/[CH:34]=[CH:35]\[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=O.C(O)[CH2:42][CH:43]([OH:48])[CH2:44][CH2:45][CH2:46][OH:47].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:5]([C:4]1([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33]/[CH:34]=[CH:35]\[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[O:48][CH:43]([CH2:44][CH2:45][CH2:46][OH:47])[CH2:42][CH2:1][O:3]1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]Participants
5
Procedure
A mixture of dilinoleyl ketone (III, 1.80 g, 3.4 mmol), 1,3,6-hexanetriol (II, 0.50 g, 3.7 mmol) and pyridinium p-toluenesulfonate (100 mg, 0.40 mmol) in 120 mL of toluene was refluxed under argon for 3 hours with a Dean-Stark tube to remove water. The resulting mixture was cooled to room temperature. The organic phase was washed with water (2×50 mL), brine (50 mL), and dried over anhydrous Na2SO4. Evaporation of the solvent resulted in pale oil (2.0 g). The crude product was purified by column chromatography on silica gel (230-400 mesh, 50 mL) with 0-3% methanol gradient in dichloromethane as eluent. This afforded 0.90 g (41%) of pure IV as colourless oil.
Workup
- temperaturewas refluxed under argon for 3 hours with a Dean-Stark tube
- customto remove water
- washThe organic phase was washed with water (2×50 mL), brine (50 mL)
- dry with materialdried over anhydrous Na2SO4
- customEvaporation of the solvent
Sources & evidence
- ORD record
- ord-84f9c675741a444e801d3a0acbcd7b6e
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09186325B2
Reaction notes
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