Ethylene carbonate → HCID 22036323, compound

HRID 1789713Notes

Reaction equation

HRID 1789713 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1.C1(=O)O[CH2:13][CH2:12][O:11]1.[H-].[Na+]>CN(C=O)C.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[O:9][CH2:13][CH2:12][OH:11]

Participants

6

Reactant 3

HCID 7303Ethylene carbonateHCID 24758Sodium hydrideHCID 759283,5-Difluorophenol

Product 1

HCID 22036323HCID 22036323, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

In a sealed Pyrex tube, a mixture of 3,5-difluorophenol (2.19 g, 16.8 mmol), ethylene carbonate (1.0 g, 11.4 mmol), a catalytic amount of NaH (60% in mineral oil) in DMF (1 mL) was reacted in a Labwell MW-10 microwave reactor at 50 W for 3 min. The reaction mixture was diluted with toluene and washed with 5% aqueous NaOH. The organic phase was dried (MgSO4) and concentrated: This gave 1.59 g (80%) of the title compound as a light red oil. MS m/z 174 (M)+.

Workup

  1. washwashed with 5% aqueous NaOH
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-52e4b5815c4948f394927bfebd82e2b9
Source dataset
uspto-grants-2006_07
Patent number
US07071180B2

Reaction notes

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