Water → HCID 70983867, compound

HRID 1852294Notes

Reaction equation

HRID 1852294 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:14].[K+].Cl[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24]Cl)[CH:19]=1.O>CS(C)=O>[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][O:14][C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7017(1,1'-Biphenyl)-2-olHCID 12275Benzene, 1,3-bis(chloromethyl)-HCID 14797Potassium Hydroxide

Product 1

HCID 70983867HCID 70983867, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
35 °C

Procedure

A 100 mL 3-neck flask was equipped with a magnetic stirrer, a reflux condenser, a nitrogen blanket, and a heating mantle with a temperature controller and a thermocouple. The flask was charged with o-phenylphenol (6.83 grams, 0.04 moles), with KOH (2.63 grams, 0.04 moles), and with 25 mL of DMSO. The mixture was stirred at about 35° C. for about ¾ hour, then a solution of α,α′-dichloro-m-xylene (3.52 grams, 0.02 moles) in 5 mL of DMSO was added to the dark solution over about 25 minutes. After the addition, the reaction mixture was heated at 50° C. for about 3 hours, and then it was poured into about 400 mL of water. A sticky white solid separated. The mixture was slurried with about 75 mL of diethyl ether; the solids dissolved. The mixture was transferred to a separatory funnel, and the layers were separated. The aqueous layer was extracted with 2×75 mL of diethyl ether. The ether layers were combined and were washed with 1×75 mL of saturated aqueous sodium chloride solution, and then they were dried over anhydrous magnesium sulfate. After filtration, the ether was removed by rotary evaporation at a bath temperature of about 60° C./P=3.4 kPa to give 8.42 grams of clear, viscous brown oil. Yield=95%. Structure was confirmed by IR, GC/MS, and 1H- and 13C-NMR analyses.

Workup

  1. customA 100 mL 3-neck flask was equipped with a magnetic stirrer, a reflux condenser
  2. additionAfter the addition
  3. temperaturethe reaction mixture was heated at 50° C. for about 3 hours
  4. customA sticky white solid separated
  5. dissolutionthe solids dissolved
  6. customThe mixture was transferred to a separatory funnel
  7. customthe layers were separated
  8. extractionThe aqueous layer was extracted with 2×75 mL of diethyl ether
  9. washwere washed with 1×75 mL of saturated aqueous sodium chloride solution
  10. dry with materialthey were dried over anhydrous magnesium sulfate
  11. filtrationAfter filtration
  12. customthe ether was removed by rotary evaporation at a bath temperature of about 60° C./P=3.4 kPa
  13. customto give 8.42 grams of clear, viscous brown oil

Sources & evidence

ORD record
ord-958d49ef34b94423b4b5a02e9910253d
Source dataset
uspto-grants-2015_02
Patent number
US08961624B2

Reaction notes

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