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

HRID 247229

Reaction equation

HRID 247229 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].[Br-].[NH4+]>C(Cl)Cl.O>[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 4

HCID 80571-BromopentaneHCID 14798Sodium HydroxideHCID 25514Ammonium BromideHCID 93939Methanone, (2-hydroxy-5-nonylphenyl)phenyl-

Product 1

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

Reagents, catalysts & solvents 2

HCID 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-butylv ammonium 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-057f14089c794352b92e158120ec2c65
Source dataset
uspto-grants-1987_11
Patent number
US04705896

Linked notes

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