1-Bromopentane → 2-n-Pentoxy-5-nonyl benzophenone

HRID 483071

Reaction equation

HRID 483071 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+].[CH2:27](Br)[CH2:28][CH2:29][CH2:30][CH3:31]>C(Cl)Cl.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:27]([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])[CH2:28][CH2:29][CH2:30][CH3:31]

Participants

7

Reactant 3

HCID 80571-BromopentaneHCID 14798Sodium HydroxideHCID 93939Methanone, (2-hydroxy-5-nonylphenyl)phenyl-

Product 1

HCID 538938732-n-Pentoxy-5-nonyl benzophenoneYield 82%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-hydroxy-5-nonyl benzophenone, 15 g, in 100 mL methylene chloride was mixed with a solution of 9.25 g NaOH in 100 mL water. To this mixture was added 6.9 g n-pentyl bromide and 1.48 g tetra-n-butylammonium bromide. The whole mixture was then vigorously agitated overnight at 40° C. After cooling to room temperature with 50 mL CH2Cl2. The combined methylene chloride layers were concentrated to an oil, which was taken up in 100 mL petroleum ether and washed with 100 mL water. Finally, the organic layer was dried over anhydrous magnesium sulfate and the volatiles removed under vacuum to give 15 g (82% yield) of 2-n-pentoxy-5-nonyl benzophenone.

Workup

  1. customvigorously agitated overnight
  2. customat 40° C
  3. concentrationThe combined methylene chloride layers were concentrated to an oil, which
  4. washwashed with 100 mL water
  5. dry with materialFinally, the organic layer was dried over anhydrous magnesium sulfate
  6. customthe volatiles removed under vacuum

Sources & evidence

ORD record
ord-c311d96f2e954f6182650344fbe57b25
Source dataset
uspto-grants-1986_03
Patent number
US04578250

Linked notes

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