tert-Butanol → 13,14-Dihydroxydocosanamide

HRID 2165755

Reaction equation

HRID 2165755 reaction equation
[C:1]([NH2:24])(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=C\CCCCCCCC.[C:25]([O-:28])(=O)[CH3:26].C([N+]([CH2:36][CH3:37])(CC)CC)C.[C:38](OO)([CH3:41])([CH3:40])C.S([O-])(O)=[O:45].[Na+].[CH3:49][C:50](O)(C)C>[Os](=O)(=O)(=O)=O.CC(C)=O>[OH:45][CH:13]([CH:25]([OH:28])[CH2:26][CH2:49][CH2:50][CH2:40][CH2:38][CH2:41][CH2:36][CH3:37])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([NH2:24])=[O:23]

Participants

8

Reactant 5

HCID 6386tert-ButanolHCID 6410tert-Butyl hydroperoxideHCID 102017Tetraethylammonium acetateHCID 5365371ErucamideHCID 23665763Sodium Bisulfite

Product 1

HCID 1508582013,14-DihydroxydocosanamideYield 33%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

Procedure

To an acetone (150 ml) solution consisting of erucamide (2 g), tetraethyl ammonium acetate (250 mg) and a 70% aqueous solution (1.3 ml) of t-BuOOH was added a 0.5% t-BuOH solution (0.5 ml) of osmium tetraoxide. The mixture was stirred at room temperature for five days. To the reaction mixture was added a 10% solution of sodium hydrogensulfite (30 ml), and the mixture was stirred for 30 minutes. The reaction mixture was subjected to filtration to collect crystals, then the crystals were washed with acetone, followed by drying to afford colorless crystals [728 mg (yield 33%)], m.p. 153 to 154° C.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. filtrationThe reaction mixture was subjected to filtration
  3. customto collect crystals
  4. washthe crystals were washed with acetone
  5. customby drying
  6. customto afford colorless crystals [728 mg (yield 33%)], m.p. 153 to 154° C.

Sources & evidence

ORD record
ord-41c89cb4b4014742aee95083a823f141
Source dataset
uspto-grants-1990_07
Patent number
US04940730

Linked notes

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