2-Hydroxy-4-methoxybenzophenone → {4-Methoxy-2-[(prop-2-en-1-yl)oxy]phenyl}(phenyl)methanone

HRID 358382

Reaction equation

HRID 358382 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[OH-].[K+].[CH2:20](Cl)[CH:21]=[CH2:22].[I-].[K+]>O1CCCC1>[CH2:22]([O:1][C:2]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])[CH:21]=[CH2:20]

Participants

6

Reactant 4

HCID 46322-Hydroxy-4-methoxybenzophenoneHCID 4875Potassium IodideHCID 7850Allyl chlorideHCID 14797Potassium Hydroxide

Product 1

HCID 14227056{4-Methoxy-2-[(prop-2-en-1-yl)oxy]phenyl}(phenyl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Hydroxy-4-methoxybenzophenone (114 parts) was dissolved in tetrahydrofuran (100 parts). Potassium hydroxide (30.9 parts) was added. By heating and stirring, complete dissolution was achieved. Allyl chloride (46.4 parts) and potassium iodide (4.2 parts) were added to this solution, which was then heated and refluxed for 8 hours. After cooling, it was washed with water and the solvent was removed by distillation. A crude product of the desired 2-allyloxy-4-methoxybenzophenone was obtained. It was recrystallized in n-hexane to obtain 125 parts of 2-allyloxy-4-methoxybenzophenone (melting point 40° C.) at 93% yield.

Workup

  1. temperatureBy heating
  2. dissolutioncomplete dissolution
  3. temperaturewas then heated
  4. temperaturerefluxed for 8 hours
  5. temperatureAfter cooling
  6. washit was washed with water
  7. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-b194dbbb179640d88942b8ef085f31a9
Source dataset
uspto-grants-1984_08
Patent number
US04467082

Linked notes

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