Toluene → HCID 10614463, compound

HRID 2295146Notes

Reaction equation

HRID 2295146 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[C:19]1([CH3:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(Cl)C1C=CC=CC=1>O.C1(C)C=CC=CC=1.CO>[CH2:25]([O:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 691504,4'-Dihydroxybenzophenone

Product 1

HCID 10614463HCID 10614463, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21867641Toluene methanolSolvent

Conditions

Temperature
80 °C

Procedure

Combine 4,4'dihydroxybenzophenone (21.4 g, 0.10 mmol) and sodium hydroxide (4.0 g, 0.10 mmol) in water (50 mL). Heat to 80° C. Add toluene (100 mL). Add benzyl chloride (17.3 mL, 0.15 mmol) in toluene/methanol (100 mL/40 mL). Maintain heating at 70° C. to 80° C. After 3 days, cool to ambient temperature and partition the reaction mixture between ethyl acetate and water. Separate the layers and extract the aqueous layer with ethyl acetate. Combine the organic layers and extract with aqueous 1M sodium hydroxide solution and then water. Evaporate the organic layers in vacuo to give a reside. Combine the aqueous layers and allow to stand to give a solid. Collect the solid by filtration, rinse with water, and dry to give a solid. Combine the solid and the residue obtained from evaporation of the organic layers and recrystallize from toluene to give 4-benzyloxy-4'-hydroxybenzophenone: Rf =0.21 (silica gel, 30% ethyl acetate/hexane).

Workup

  1. temperatureMaintain
  2. temperatureheating at 70° C. to 80° C
  3. temperaturecool to ambient temperature
  4. custompartition the reaction mixture between ethyl acetate and water
  5. customSeparate the layers
  6. extractionextract the aqueous layer with ethyl acetate
  7. extractionextract with aqueous 1M sodium hydroxide solution
  8. customEvaporate the organic layers in vacuo
  9. customto give a reside
  10. customto give a solid
  11. customCollect the solid
  12. filtrationby filtration
  13. washrinse with water
  14. customdry
  15. customto give a solid
  16. customthe residue obtained from evaporation of the organic layers
  17. customrecrystallize from toluene

Sources & evidence

ORD record
ord-09a6dcbfb9c144aeadaaae4b6628ccab
Source dataset
uspto-grants-1997_11
Patent number
US05691384

Reaction notes

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