Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2,2-Dilinoleyl-4-(2-hydroxyethyl)-[1,3]-dioxane

HRID 713852Notes

Reaction equation

HRID 713852 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.[CH2:41]([OH:48])[CH2:42][CH:43]([OH:47])[CH2:44]CO.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:47][CH:43]([CH2:42][CH2:41][OH:48])[CH2:44][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

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 5543631,3,5-PentanetriolHCID 58264324Dilinoleylmethyl Formate

Product 1

HCID 585595812,2-Dilinoleyl-4-(2-hydroxyethyl)-[1,3]-dioxaneYield 116.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of dilinoleyl ketone (III, 0.80 g, 1.5 mmol), 1,3,5-pentanetriol (II, 0.54 g, 4.5 mmol) and pyridinium p-toluenesulfonate (60 mg, 0.24 mmol) in 150 mL of toluene was refluxed under nitrogen overnight with a Dean-Stark tube to remove water. The resulting mixture was cooled to room temperature. The organic phase was washed with water (2×75 mL), brine (75 mL), and dried over anhydrous Na2SO4. Evaporation of the solvent resulted in pale oil (1.1 g). The crude product was purified by column chromatography on silica gel (230-400 mesh, 75 mL) with 0-3% methanol gradient in dichloromethane as eluent. This afforded 0.75 g (79%) of pure IV as colourless oil.

Workup

  1. temperaturewas refluxed under nitrogen overnight with a Dean-Stark tube
  2. customto remove water
  3. washThe organic phase was washed with water (2×75 mL), brine (75 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-0d4c01292af34d14bb1a0198e7ebd62a
Source dataset
uspto-grants-2015_11
Patent number
US09186325B2

Reaction notes

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