(+-)-1,2,5-Pentanetriol → 2,2-Dilinoleyl-4-(3-hydroxypropyl)-[1,3]-dioxolane

HRID 2280990Notes

Reaction equation

HRID 2280990 reaction equation
[CH2:1]([C:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31]/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:39](O)[CH:40]([OH:45])[CH2:41][CH2:42][CH2:43][OH:44].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([C:19]1([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31]/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[O:45][CH:40]([CH2:41][CH2:42][CH2:43][OH:44])[CH2:39][O:20]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 85763(+-)-1,2,5-PentanetriolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 59544992Bis(linoleyl) ketone

Product 1

HCID 584732522,2-Dilinoleyl-4-(3-hydroxypropyl)-[1,3]-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of dilinoleyl ketone (I, previously prepared as described in Example 1, 1.0 g, 2 mmol), 1,2,5-pentanetriol (crude, 0.25 g, 2 mmol) and pyridinium p-toluenesulfonate (100 mg, 0.4 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 (3×40 mL), brine (50 mL), and dried over anhydrous Na2SO4. Evaporation of the solvent gave a yellowish oily residual (1.1 g). The crude product was purified by column chromatography on silica gel (230-400 mesh, 100 mL) with 0-1% methanol in dichloromethane as eluent. This afforded 0.90 g of pure II as colourless oil.

Workup

  1. custompreviously prepared
  2. temperaturewas refluxed under nitrogen overnight with a Dean-Stark tube
  3. customto remove water
  4. washThe organic phase was washed with water (3×40 mL), brine (50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customEvaporation of the solvent
  7. customgave a yellowish oily residual (1.1 g)
  8. customThe crude product was purified by column chromatography on silica gel (230-400 mesh, 100 mL) with 0-1% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-e1be89fda516483e81b8e91f058d35ed
Source dataset
uspto-grants-2015_09
Patent number
US09139554B2

Reaction notes

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