Sodium periodate → HCID 86587292, compound

HRID 580808Notes

Reaction equation

HRID 580808 reaction equation
[OH:1][CH:2](CO)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][O:15][C:16](=[O:29])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([OH:28])CO)=[O:12].I([O-])(=O)(=O)=O.[Na+]>O1CCCC1.O>[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][O:15][C:16](=[O:29])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[O:28])=[O:12]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 86587293HCID 86587293, compound

Product 1

HCID 86587292HCID 86587292, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Methylene bis(10,11-dihydroxyundecanoate) (2.24 g, 5 mmol) was dissolved in 150 ml tetrahydrofuran. Sodium metaperiodate (2.06 g, 10 mmol) was dissolved in 150 ml water and added dropwise to the tetrahydrofuran solution. TLC indicated full consumption of the diol after 60 minutes, whereupon sodium chloride was added to the reaction mixture until the two phases separated. The water phase was extracted with diethyl ether (3×50 ml). The combined organic phases were dried with magnesium sulphate and evaporated to give the title product as an oil, 1.43 g (74%). 13C NMR (45 MHz) CDCl3 : δ 21.9-43.9 (16×CH2), 79.1 (O--CH2 --O), 173.0 (2×C=O), 202.6 (2×CHO).

Workup

  1. customconsumption of the diol after 60 minutes
  2. additionwhereupon sodium chloride was added to the reaction mixture until the two phases
  3. customseparated
  4. extractionThe water phase was extracted with diethyl ether (3×50 ml)
  5. dry with materialThe combined organic phases were dried with magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-dcad29b0df864cb3b70c53aefd270646
Source dataset
uspto-grants-1999_07
Patent number
US05919753

Reaction notes

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