Diethylene Glycol → HCID 18975523, compound

HRID 2393294Notes

Reaction equation

HRID 2393294 reaction equation
C(O)[CH2:2][O:3][CH2:4][CH2:5][OH:6].[OH-:8].[K+].BrC(Br)=C[C:13]1[CH:18]=[C:17]([Br:19])[CH:16]=[C:15]2[O:20]CO[C:14]=12>O>[Br:19][C:17]1[CH:16]=[C:4]2[O:3][CH2:2][O:6][C:5]2=[C:13]([CH2:14][C:15]([OH:20])=[O:8])[CH:18]=1

Participants

5

Reactant 3

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 18975515HCID 18975515, compound

Product 1

HCID 18975523HCID 18975523, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diethylene glycol (100 ml), water (60 ml), and 85% potassium hydroxide (32 g, 0.485 mol) were added to β, β-dibromo-5-bromo-2,3-methylenedioxystyrene (42.36 g, 0.11 mol), and the mixture was heated with stirring under reflux for 2 hours. The reaction mixture was poured into ice water and extracted with toluene. The extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was recrystallized from ethyl acetate (80 ml) and hexane (300 ml) to give 5-bromo-2,3-methylenedioxyphenylacetic acid (25.35 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with toluene
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was recrystallized from ethyl acetate (80 ml) and hexane (300 ml)

Sources & evidence

ORD record
ord-12be7600b92f461fb53810ee93fbbe18
Source dataset
uspto-grants-1998_09
Patent number
US05807860

Reaction notes

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