Sodium periodate → HCID 86587292, compound

HRID 260627Notes

Reaction equation

HRID 260627 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 was 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 was dried with magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-1b795d1cf68243baaaf7095832b8441e
Source dataset
uspto-grants-1996_06
Patent number
US05529766

Reaction notes

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