Phenol → Allyl phenyl ether

HRID 2208625Notes

Reaction equation

HRID 2208625 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[C:10](Cl)(=O)[CH:11]=[CH2:12]>CC(C)=O>[C:1]1([O:7][CH2:12][CH:11]=[CH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 13140Acryloyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 74458Allyl phenyl etherYield 99.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into a reaction vessel equipped with a stirrer, thermometer, and reflux condenser 94 g (1.0 mol) of phenol, 40 g (1.0 mol) of NaOH, and 210 g of acetone were introduced. With stirring the contents, the internal temperature was elevated to 40° C. Subsequently, 76 g (1.0 mol) of acryloyl chloride was added dropwise thereto over 1 hour. After completion of the dropwise addition, the reaction mixture was further kept at 40° C. for 2 hours and reacted thereby. The reaction product was filtered to remove the NaCl yielded as a by-product, and the acetone was thereafter removed under reduced pressure to obtain 134 g of allyl phenyl ether.

Workup

  1. customInto a reaction vessel equipped with a stirrer
  2. additionwere introduced
  3. customwas elevated to 40° C
  4. additionAfter completion of the dropwise addition
  5. waitthe reaction mixture was further kept at 40° C. for 2 hours
  6. customreacted
  7. filtrationThe reaction product was filtered
  8. customto remove the NaCl
  9. customyielded as a by-product
  10. customthe acetone was thereafter removed under reduced pressure

Sources & evidence

ORD record
ord-174fa0a1298a4f10878ba3eba94fb175
Source dataset
uspto-grants-2016_06
Patent number
US09376510B2

Reaction notes

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