Water → 2-Methoxy-5-nonyl benzophenone

HRID 247227

Reaction equation

HRID 247227 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[OH-].[Na+].O.I[CH3:29]>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:29][O:1][C:2]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 93939Methanone, (2-hydroxy-5-nonylphenyl)phenyl-

Product 1

HCID 201619912-Methoxy-5-nonyl benzophenoneYield 85%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A sample of 2-hydroxy-5-nonyl benzophenone (25 g, 0.077 mol) was dissolved in 100 mL methylene chloride. To this solution was added a solution of 20 g (0.5 mol) sodium hydroxide in 100 mL deionized water, followed by the addition of 22 g (0.154 mol) iodomethane and 2.5 g (0.006 mol) tetra-n-butylammonium bromide. The entire mixture was agitated with vigorous mechanical stirring for 1.5 hours at 45° C. The reaction mixture was allowed to cool, and the layers separated. The aqueous phase was extracted with 50 mL methylene chloride. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated under vacuum. The residual oil was taken up in petroleum ether, washed with water, dried over magnesium sulfate and again concentrated under vacuum to provide 22 g (85% yield) of 2-methoxy-5-nonyl benzophenone.

Workup

  1. stirringmechanical stirring for 1.5 hours at 45° C
  2. temperatureto cool
  3. customthe layers separated
  4. extractionThe aqueous phase was extracted with 50 mL methylene chloride
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationagain concentrated under vacuum

Sources & evidence

ORD record
ord-02cf0dcdccc24239a71a435376af0989
Source dataset
uspto-grants-1987_11
Patent number
US04705896

Linked notes

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