Dimethyl Sulfoxide → 2-(Hexadecyloxy)-1,1'-biphenyl

HRID 1852295Notes

Reaction equation

HRID 1852295 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-].[K+].CS(C)=O.Cl[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>O>[CH2:36]([O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH3:21]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7017(1,1'-Biphenyl)-2-olHCID 14797Potassium Hydroxide2×HCID 209931-Chlorohexadecane

Product 1

HCID 709842442-(Hexadecyloxy)-1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °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 (3.42 grams, 0.02 moles), with KOH pellets (1.37 grams, 0.02 moles, 85%), and with 15 mL of DMSO. The mixture was stirred at 100° C. under nitrogen until all of the KOH had dissolved (about 2 hours). The dark solution was cooled to 70° C., then the 1-chlorohexadecane (5.22 grams, 0.02 moles) was then added all at once. An exotherm to about 80° C. was observed. The reaction mixture was then stirred at 75° C. for about 7.5 hours, then it was poured into about 500 mL of water; solids separated.

Workup

  1. customA 100 mL 3-neck flask was equipped with a magnetic stirrer, a reflux condenser
  2. dissolutionhad dissolved (about 2 hours)
  3. customto about 80° C.
  4. customsolids separated

Sources & evidence

ORD record
ord-7b54ba71f95f413eac48e35dba1ba267
Source dataset
uspto-grants-2015_02
Patent number
US08961624B2

Reaction notes

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