4-Nonylphenol → 1-Methoxy-4-nonylbenzene

HRID 247230Notes

Reaction equation

HRID 247230 reaction equation
[CH2:1]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[OH-].[K+].I[CH3:20]>C(Cl)Cl.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:20])=[CH:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

7

Reactant 3

HCID 17524-NonylphenolHCID 6328Methyl iodideHCID 14797Potassium Hydroxide

Product 1

HCID 40496921-Methoxy-4-nonylbenzeneYield 84%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of p-nonylphenol, 35 g, in 125 mL methylene chloride was mixed with a solution of 44.5 g KOH in 125 mL water. To this mixture was added 45 g iodomethane and 5.0 g tetra-n-butylammonium bromide. The whole mixture was vigorously stirred at 40° C. for one hour. After cooling to room temperature, the phases were separated and the aqueous phase extracted with 50 mL methylene chloride. The combined methylene chloride layers were concentrated to an oil which was taken up in 200 mL of petroleum ether and filtered to remove the residual phase transfer catalyst. Finally, the petroleum ether was removed under vacuum to give 31.1 g (84%) of p-nonylanisole.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe phases were separated
  3. extractionthe aqueous phase extracted with 50 mL methylene chloride
  4. concentrationThe combined methylene chloride layers were concentrated to an oil which
  5. filtrationfiltered
  6. customto remove the residual phase transfer catalyst
  7. customFinally, the petroleum ether was removed under vacuum

Sources & evidence

ORD record
ord-dad8bb10ef4f404886653685e66b3e5c
Source dataset
uspto-grants-1987_11
Patent number
US04705896

Reaction notes

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