Ethylene carbonate → HCID 13939035, compound

HRID 1073409Notes

Reaction equation

HRID 1073409 reaction equation
[CH3:1][CH:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH2:3][CH3:4].C1(=O)O[CH2:16][CH2:15][O:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][CH:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:16][CH2:15][OH:14])=[CH:10][CH:11]=1)[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 7303Ethylene carbonateHCID 11430Potassium Carbonate2×HCID 138820044-(1-Methyl-1-propyloxy)-phenol

Product 1

HCID 13939035HCID 13939035, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(1-Methylpropoxy)phenol (6.92 g, 41.6 mmol), ethylene carbonate (7.34 g, 83.2 mmol) and DMF (45 ml) are mixed under N2. With stirring, the mixture is degassed (3×) by alternate application of vacuum and N2. Potassium carbonate (11.51 g, 83.2 mmol) is then added, under N2, and the mixture is heated at 90° for 27 hours. The reaction mixture is then poured into ice water and 10 ml of 40% potassium carbonate solution is added to increase the pH to 13. The aqueous phase is extracted with ether (3×) and the organic layers are washed with 40% KOH, the water until neutral and with brine, dried, filtered and the solvent evaporated to give 2-[4-(1-methylpropoxy)phenoxy]ethanol.

Workup

  1. customthe mixture is degassed (3×) by alternate application of vacuum and N2
  2. temperaturethe mixture is heated at 90° for 27 hours
  3. additionis added
  4. temperatureto increase the pH to 13
  5. extractionThe aqueous phase is extracted with ether (3×)
  6. washthe organic layers are washed with 40% KOH
  7. dry with materialthe water until neutral and with brine, dried
  8. filtrationfiltered
  9. customthe solvent evaporated

Sources & evidence

ORD record
ord-a65b7c0f143b4936ab281b3579a876f8
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

Loading…