Phenol → Phenoxyethanol

HRID 1759592Notes

Reaction equation

HRID 1759592 reaction equation
[C:1]1(=O)[O:5][CH2:4][CH2:3][O:2]1.[C:7]1(O)[CH:12]=[CH:11]C=[CH:9][CH:8]=1>[F-].[K+]>[O:2]([CH2:3][CH2:4][OH:5])[C:1]1[CH:11]=[CH:12][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 996PhenolHCID 7303Ethylene carbonate

Product 1

HCID 31236PhenoxyethanolYield 99.2%

Reagents, catalysts & solvents 1

HCID 522689Potassium FluorideCatalyst

Procedure

Ethylene carbonate (89.9 g, 1.02 mole), phenol (94.1 g, 1.0 mole) and potassium fluoride (1 g, 0.5 percent of total reactant weight) were placed in a 500 ml round-bottomed flask equipped with a condenser and gas bubbler. A magnetic stirrer provided agitation. The mixture was heated to 160° C.±2° C. in an oil bath. After 2.5 hours the reaction vessel was removed from the oil bath, cooled and the contents removed. Purification of the product by distillation gave 137 g of 2-phenoxyethanol (99 percent conversion based on phenol limiting reagent).

Workup

  1. customequipped with a condenser
  2. customA magnetic stirrer provided agitation
  3. temperatureThe mixture was heated to 160° C.±2° C. in an oil bath
  4. customAfter 2.5 hours the reaction vessel was removed from the oil bath
  5. temperaturecooled
  6. customthe contents removed
  7. customPurification of the product
  8. distillationby distillation

Sources & evidence

ORD record
ord-880fa754d99c40a5a3f1bbe5811f369c
Source dataset
uspto-grants-1982_07
Patent number
US04341905

Reaction notes

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