Potassium Hydroxide → 4-Vinylphenol

HRID 1447476Notes

Reaction equation

HRID 1447476 reaction equation
C([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1)(=O)C.[OH-].[K+]>O>[CH:9]([C:8]1[CH:11]=[CH:12][C:5]([OH:4])=[CH:6][CH:7]=1)=[CH2:10]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 758214-Ethenylphenyl acetate2×

Product 1

HCID 624534-Vinylphenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 2 liter reaction flask equipped with cooling bath, heating mantle, electric stirrer, thermometer and addition funnel is placed 129 grams of paraacetoxy styrene produced according to Example IV(B) and a solution of 112 grams of potassium hydroxide in 1120 ml water. The resulting reaction mass is heated to 35°-40° C. until all the paraacetoxy styrene is consumed by the base. This takes approximately 45 minutes. The reaction mass is then cooled to 20°-25° C. and over a period of 0.5 hours, enough 10% aqueous acetic acid is added to the reaction mass to bring the pH to 6 (630 ml 10% aqueous acetic acid added). At this point, 75 grams of crystals precipitate. The crystals are washed with 150 ml water and air dried to yield food grade, substantially pure paravinyl phenol.

Workup

  1. customInto a 2 liter reaction flask
  2. customequipped
  3. temperaturewith cooling bath
  4. temperatureheating mantle, electric stirrer
  5. additionthermometer and addition funnel
  6. customproduced
  7. customThe resulting reaction mass
  8. customis consumed by the base
  9. customThis takes approximately 45 minutes
  10. temperatureThe reaction mass is then cooled to 20°-25° C. and over a period of 0.5 hours
  11. additionenough 10% aqueous acetic acid is added to the reaction mass
  12. additionto 6 (630 ml 10% aqueous acetic acid added)
  13. washThe crystals are washed with 150 ml water and air
  14. customdried

Sources & evidence

ORD record
ord-0e3b0a4363b34de1af3b3333cc07ac17
Source dataset
uspto-grants-1982_02
Patent number
US04316995

Reaction notes

Loading…