1,5-Dibromopentane → HCID 19761051, compound

HRID 249274Notes

Reaction equation

HRID 249274 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-75b54ce189ba498cb24960bc57f8fe8d
Source dataset
uspto-grants-1993_05
Patent number
US05214046

Reaction notes

Loading…