Ethylene carbonate → HCID 13939035, compound

HRID 2309828Notes

Reaction equation

HRID 2309828 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)C=O>[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 dimethylformamide (DMF; 45 ml) are mixed under N2. With stirring, the mixture is degassed (3X) 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 (3X) and the organic layers are washed with 40% KOH, with 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 (3X) 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 (3X)
  6. washthe organic layers are washed with 40% KOH, with water until neutral and with brine
  7. customdried
  8. filtrationfiltered
  9. customthe solvent evaporated

Sources & evidence

ORD record
ord-56fc5adaa8be4080a8a623fea754347f
Source dataset
uspto-grants-1987_09
Patent number
US04697033

Reaction notes

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