Glycidol → HCID 22380685, compound

HRID 895613Notes

Reaction equation

HRID 895613 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[C:4]([C:6]1[CH:19]=[CH:18][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[OH-].[Na+].[CH2:24]1[O:26][CH:25]1[CH2:27][OH:28]>O1CCOCC1.O>[CH2:20]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:19]=[CH:18][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH2:24][CH:25]([OH:26])[CH2:27][OH:28])=[CH:8][CH:7]=1)=[O:5])[CH3:21]

Participants

6

Reactant 3

HCID 11164GlycidolHCID 14798Sodium HydroxideHCID 223807182-(4-Diethylcarbamoylbenzyl)phenol

Product 1

HCID 22380685HCID 22380685, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

The 2-(4-diethylcarbamoylbenzyl)phenol (355 mg) obtained in Reference Example 1(d) was dissolved in a mixed solution of dioxane (3.6 ml) and water (3.6 ml), added with 1 N aqueous sodium hydroxide (63 μl) and glycidol (0.12 ml) and stirred at 90° C. for 18 hours. The reaction mixture was added with water (30 ml) and extracted twice with dichloromethane (30 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate) to obtain 263 mg of the title compound. Yield: 59%.

Workup

  1. extractionextracted twice with dichloromethane (30 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate)

Sources & evidence

ORD record
ord-9edc131eb50e4283a41ff2d9bbd18871
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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