1,5-Dibromopentane → HCID 19761051, compound

HRID 1030666Notes

Reaction equation

HRID 1030666 reaction equation
[OH-].[Na+].Br[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][Br:9].[OH:10][C:11]1[CH:24]=[CH:23][C:14]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])=[CH:13][CH:12]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Br:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 81001,5-DibromopentaneHCID 143474-HydroxybenzophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 19761051HCID 19761051, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

100 ml of a 10 percent aqueous sodium hydroxide solution were added to a solution of 34.5 g of 1.5-dibromopentane, 9.9 g of 4-hydroxybenzophenone and 1.6 g of tetrabutylammonium bromide in 100 ml of methylene chloride. The heterogeneous mixture was stirred at room temperature overnight. The organic phase was separated, dried over sodium sulphate and evaporated. By chromatography of the residue on silica gel with hexane:ethyl acetate 7:3) there were obtained 13.47 g (78%) of 4-[(5-bromopentyl)oxy]benzophenone as a colorless oil.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-702fb80dc0f54d4585334a058866e66e
Source dataset
uspto-grants-1992_04
Patent number
US05106878

Reaction notes

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