Epichlorohydrin → HCID 22386937, compound

HRID 490327Notes

Reaction equation

HRID 490327 reaction equation
[CH3:1][C:2]1[C:3]([NH:9][C:10](=[O:12])[CH3:11])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH2:13]([CH:15]1[O:17][CH2:16]1)Cl.[OH-].[Na+].CCOC(C)=O>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.CCCCCCC>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:13][CH:15]2[CH2:16][O:17]2)[C:3]=1[NH:9][C:10](=[O:12])[CH3:11]

Participants

7

Reactant 4

HCID 7835EpichlorohydrinHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 153835Acetamide, N-(2-hydroxy-6-methylphenyl)-

Product 1

HCID 22386937HCID 22386937, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8900HeptaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-methyl-2-acetamidophenol (0.165 g, 1 mmol), and epichlorohydrin (1.84 g, 20 mmol) was stirred at 70° C. to afford a clear solution. Triethylbenzylammonium chloride (0.15 g, 1 mmol) was then added and stirring was continued at 125° C. for 15 minutes. After cooling to room temperature 1M NaOH solution was added and the solution was extracted with dichloromethane. The organic extract was washed with water and dried. After evaporation of the dichloromethane the resulting brownish oil was purified through silica chromatography 50-70% EtOAc in heptane yielding the product as a colourless oil (0.12 g, 0.54 mmol).

Workup

  1. customto afford a clear solution
  2. stirringstirring
  3. additionwas added
  4. extractionthe solution was extracted with dichloromethane
  5. extractionThe organic extract
  6. washwas washed with water
  7. customdried
  8. customAfter evaporation of the dichloromethane the resulting brownish oil

Sources & evidence

ORD record
ord-03cf93bbbd2a49eb89c31bb9ad2462a9
Source dataset
uspto-grants-2009_05
Patent number
US07528156B2

Reaction notes

Loading…