Dimethyl Sulfoxide → HCID 70984102, compound

HRID 1852296Notes

Reaction equation

HRID 1852296 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+].CS(C)=O.Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br>C(OCC)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][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:14][C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7017(1,1'-Biphenyl)-2-olHCID 123681,6-DibromohexaneHCID 14797Potassium Hydroxide

Product 1

HCID 70984102HCID 70984102, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
35 °C

Procedure

A 250 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 (6.81 grams, 0.04 moles), with KOH pellets (2.64 grams, 0.04 moles, 85%), and with 50 mL of DMSO. The mixture was stirred at about 35° C. for about 1½ hours, then 1,6-dibromohexane (4.88 grams, 0.02 moles) was added in one portion. The reaction mixture was stirred at about 75° C. for about 2 hours, then it was poured into about 500 mL of water. A milky white suspension formed. The mixture was slurried with about 100 mL of diethyl ether, then it was transferred to a separatory funnel. The layers were separated, and the aqueous layer was extracted with 5×100 mL of diethyl ether. The ether layers were combined, and were washed with 1×100 mL of water and with 1×100 mL of saturated aqueous sodium chloride. After drying the ether solution over anhydrous magnesium sulfate, the solution was filtered, and the solvent was removed by rotary evaporation at a bath temperature of about 60° C./P=3.4 kPa. The yield of product was 7.06 grams (84%) as a white solid having mp=92-95° C. Structure was confirmed by IR, GC/MS, and 1H- and 13C-NMR analyses.

Workup

  1. customA 250 mL 3-neck flask was equipped with a magnetic stirrer, a reflux condenser
  2. stirringThe reaction mixture was stirred at about 75° C. for about 2 hours
  3. customA milky white suspension formed
  4. customit was transferred to a separatory funnel
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with 5×100 mL of diethyl ether
  7. washwere washed with 1×100 mL of water and with 1×100 mL of saturated aqueous sodium chloride
  8. dry with materialAfter drying the ether solution over anhydrous magnesium sulfate
  9. filtrationthe solution was filtered
  10. customthe solvent was removed by rotary evaporation at a bath temperature of about 60° C./P=3.4 kPa

Sources & evidence

ORD record
ord-ed064218962d4fa2a9f2a1d0ad6eec80
Source dataset
uspto-grants-2015_02
Patent number
US08961624B2

Reaction notes

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