Carbon Dioxide → 2-(1,3-Benzodioxol-4-yloxy)ethanol

HRID 991678

Reaction equation

HRID 991678 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([OH:10])[C:4]=2[O:3][CH2:2]1.C1(=O)O[CH2:14][CH2:13][O:12]1.C([O-])([O-])=O.[K+].[K+].C(=O)=O>CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([O:10][CH2:14][CH2:13][OH:12])[C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 5867271,3-Benzodioxol-4-ol

Product 1

HCID 220365462-(1,3-Benzodioxol-4-yloxy)ethanolYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1,3-benzodioxol-4-ol* (0.74 g, 5.36 mmol), ethylene carbonate (0.47 g, 5.3 mmol) and K2CO3 (0.67 g, 4.8 mmol) in DMF (30 mL) was heated at 150° C. After the evolution of carbon dioxide had ceased (1 h), the reaction mixture was filtered and concentrated. The crude product was purified by chromatography on silica gel using petroleum ether/EtOAc (70:30) as eluent to give 0.64 g (65%) of the title product as an oil which spontaneously crystallized to a white solid: mp 56-57° C. Anal. (C9H10O4) C, H.

Workup

  1. custom(1 h)
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated
  4. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-6cee3048f6d7449194d73f8ab145497b
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Linked notes

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