Dimethyl Sulfoxide → HCID 86718394, compound

HRID 1509355Notes

Reaction equation

HRID 1509355 reaction equation
[C:1]1([OH:14])[C:2]([C:7]2[C:8]([OH:13])=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:3][CH:4]=[CH:5][CH:6]=1.[OH-].[K+].CS(C)=O.[CH2:21](Br)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>O>[CH2:21]([O:14][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:7][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:1])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 89191-BromododecaneHCID 14797Potassium Hydroxide2×HCID 15731(1,1'-Biphenyl)-2,2'-diol

Product 1

HCID 86718394HCID 86718394, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 100 mL 3-neck flask was equipped with a magnetic stirrer, a reflux condenser with nitrogen blanket, and a heating mantle with a temperature controller and a thermocouple. The flask was charged with 3.74 grams (0.02 moles) of 2,2′-biphenol, 2.8 grams (0.04 moles, 85 wt. %) of potassium hydroxide, and with 25 mL of dimethylsulfoxide. The mixture was stirred under nitrogen while heating to 100° C. After about 2½ hours, the potassium hydroxide had dissolved, and the mixture was cooled to about 70° C. Dodecyl bromide (9.60 mL; d 1.038; 9.97 grams; 0.04 moles) was added in one portion. An exotherm to about 86° C. was observed. After the exotherm subsided, the reaction mixture was stirred at 70° C. After about 5 hours, the reaction mixture was poured into about 400 mL of water. The white solids that separated were collected by filtration, and were washed on the filter with several portions of water. The solids were first air-dried, and then were dried in a vacuum oven at 50° C. for about 2 hours. The yield of product was 9.49 grams (91%), having a melting point of 33-35° C. The structure was confirmed by IR, 1H- and 13C-NMR, and GC/MS analyses.

Workup

  1. customA 100 mL 3-neck flask was equipped with a magnetic stirrer, a reflux condenser with nitrogen blanket
  2. waitAfter about 2½ hours
  3. temperaturethe mixture was cooled to about 70° C
  4. customto about 86° C.
  5. stirringthe reaction mixture was stirred at 70° C
  6. customThe white solids that separated
  7. filtrationwere collected by filtration
  8. washwere washed on the
  9. filtrationfilter with several portions of water
  10. customwere dried in a vacuum oven at 50° C. for about 2 hours

Sources & evidence

ORD record
ord-53cbc67c96ac4341b203d5468f4bcae0
Source dataset
uspto-grants-2015_12
Patent number
US09222928B2

Reaction notes

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