Ethylene carbonate → 2-(p-Bromophenoxy)ethanol

HRID 2428082Notes

Reaction equation

HRID 2428082 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[O:9]1[CH2:13][CH2:12]OC1=O>N1C=CN=C1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH2:13][OH:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7303Ethylene carbonateHCID 78084-Bromophenol

Product 1

HCID 991682-(p-Bromophenoxy)ethanolYield 103.3%

Reagents, catalysts & solvents 1

HCID 795ImidazoleCatalyst

Conditions

Temperature
140 °C

Procedure

4-Bromophenol (100 g, 0.58 mol) was dissolved in in xylenes (220 mL). [1,3]Dioxolan-2-one (53.7 g, 0.61 mol) and imidazole (592 mg, 8.70 mmol) were added. The mixture was heated to 140° C. for 3 days. The mixture was allowed to cool to rt, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the title compound (130 g, quantitative). LC-MS: tR=0.81 min.

Workup

  1. temperatureto cool to rt
  2. customthe solvents were removed under reduced pressure
  3. customDrying the residue under high vacuum

Sources & evidence

ORD record
ord-5d78c3d9d80b4f8491ae8a8da838f9ab
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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