Potassium Hydroxide → HCID 90010802, compound

HRID 1481841Notes

Reaction equation

HRID 1481841 reaction equation
[C:1]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][OH:36]>CS(C)=O>[C:1]([C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][OH:36])=[CH:24][CH:25]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 704224-(Triphenylmethyl)phenolHCID 748286-Chloro-1-hexanol

Product 1

HCID 90010802HCID 90010802, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A 25 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 1.12 grams (0.0033 moles) of 4-tritylphenol, 0.22 grams (0.0033 moles, 85 wt. %) of potassium hydroxide pellets, and with 5 mL of dimethylsulfoxide. The mixture was stirred under nitrogen while heating to 100° C. After about 2 hours, all of the potassium hydroxide had dissolved, and the mixture was cooled to 70° C. 6-Chlorohexanol (0.45 grams, 0.0033 moles) was then added in one portion. The reaction mixture was maintained at 100° C. for about 0.5 hours, then it was stirred at room temperature overnight. A sample withdrawn for GC analysis at this point showed no remaining starting materials, indicating that the reaction was completed. The reaction mixture was poured into 100 mL of water. Solids precipitated. The mixture was filtered. The beige solids were washed on the filter with several portions of water, then they were air-dried. The yield of product was 1.2 grams (83%). The structure was confirmed by IR, 1H- and 13C-NMR, and GC/MS analyses.

Workup

  1. customA 25 mL 3-neck flask was equipped with a magnetic stirrer, a reflux condenser with nitrogen blanket
  2. temperaturethe mixture was cooled to 70° C
  3. temperatureThe reaction mixture was maintained at 100° C. for about 0.5 hours
  4. stirringit was stirred at room temperature overnight
  5. customA sample withdrawn for GC analysis at this point
  6. additionThe reaction mixture was poured into 100 mL of water
  7. customSolids precipitated
  8. filtrationThe mixture was filtered
  9. washThe beige solids were washed on the
  10. filtrationfilter with several portions of water
  11. customthey were air-dried

Sources & evidence

ORD record
ord-8d20844120c64cd291be7c5f87bfc188
Source dataset
uspto-grants-2016_08
Patent number
US09410100B2

Reaction notes

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