Phenol → Ether, dodecyl phenyl

HRID 1760898Notes

Reaction equation

HRID 1760898 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>CN(C=O)C>[CH2:26]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15]

Participants

5

Reactant 3

HCID 996PhenolHCID 89191-BromododecaneHCID 11430Potassium Carbonate

Product 1

HCID 294549Ether, dodecyl phenyl

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Phenol (47 g; 0.5 mol) is dissolved in DMF (300 ml), and K2CO3 (82.93 g; 0.6 mol) is added. 1-Bromododecane (124.6 g; 0.5 mol) is then added dropwise to the solution at 70° C. After a further 15 hours at 80° C., cooling to 25° C. is carried out, followed by dilution with water (500 ml) and extraction with tert-butyl methyl ether (2×250 ml). The combined organic extracts are washed with water (2×250 ml) and dried over Na2SO4. After filtration, concentration to dryness by evaporation is carried out.

Workup

  1. extractionfollowed by dilution with water (500 ml) and extraction with tert-butyl methyl ether (2×250 ml)
  2. washThe combined organic extracts are washed with water (2×250 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration, concentration to dryness
  5. customby evaporation

Sources & evidence

ORD record
ord-97f3281689274d42a408cac609aa7d02
Source dataset
uspto-grants-2005_01
Patent number
US06846492B2

Reaction notes

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