Sodium Hydroxide → HCID 58264321, compound

HRID 1259004Notes

Reaction equation

HRID 1259004 reaction equation
[CH2:1]([O:4][CH2:5][CH:6]([OH:9])[CH2:7][OH:8])[CH:2]=[CH2:3].S(O[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=O)(=O)C.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.C1(C)C=CC=CC=1>[CH2:1]([O:4][CH2:5][CH:6]([O:9][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:7][O:8][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:2]=[CH2:3]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 78950Glyceryl Allyl EtherHCID 59753235Linoleyl methanesulfonate

Product 1

HCID 58264321HCID 58264321, compoundYield 73.1%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A 500 mL round bottom flask was charged with 3-(allyloxy)propane-1,2-diol (2.6 g, 19.8 mmol), linoleyl mesylate (15.0 g, 43.5 mmol), tetrabutylammonium hydrogen sulfate (3.4 g, 9.9 mmol), toluene (600 mL) and 40% NaOH (30 mL). The reagents were vigorously stirred (emulsified) for 80 hours at room temperature. Upon completion, the solution was diluted with water (100 mL) and toluene (100 mL). The toluene was separated and the remaining aqueous solution was extracted with toluene (150 mL). The combine toluene extracts were dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography on silica gel 60 (eluted with 5% diethyl ether in hexanes) to afford (6Z,9Z)-18-(3-(allyloxy)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propoxy)octadeca-6,9-diene as a colorless oil (9.1 g, 73%).

Workup

  1. customThe toluene was separated
  2. extractionthe remaining aqueous solution was extracted with toluene (150 mL)
  3. dry with materialThe combine toluene extracts were dried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to dryness
  6. customThe residue was purified by column chromatography on silica gel 60 (eluted with 5% diethyl ether in hexanes)

Sources & evidence

ORD record
ord-95a275070e414e8a832785ec29698d20
Source dataset
uspto-grants-2013_06
Patent number
US08466122B2

Reaction notes

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