1-Propanol → HCID 19102190, compound

HRID 1974679Notes

Reaction equation

HRID 1974679 reaction equation
Br[C:2]1[C:7](=[O:8])[C:6]([Br:9])=[C:5]([Br:10])[C:4](=[O:11])[C:3]=1[Br:12].[C:13](=O)([O-])O.[Na+].[CH2:18]([OH:21])[CH2:19]C>CCC(C)=O>[Br:9][C:6]1[C:7](=[O:8])[C:2]([O:21][CH:18]([CH3:19])[CH3:13])=[C:3]([Br:12])[C:4](=[O:11])[C:5]=1[Br:10]

Participants

5

Reactant 3

HCID 10311-PropanolHCID 68101BromanylHCID 516892Sodium Bicarbonate

Product 1

HCID 19102190HCID 19102190, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Tetrabromobenzo-1,4-quinone (14.6 parts) was stirred in MEK prior to adding sodium hydrogen carbonate (5.5 parts) and stirring at room temperature. Aqueous propanol (50 parts, 1:1) was added and the reaction was monitored by HPLC until no starting material remained. The resulting solution (which contained 91% 2,3,5-tribromo-6-isopropoxy benzoquinone as judged by HPLC) was recrystallised from 60-80 petrol ether (136 ml) to yield a homogeneous crystalline product (6 parts). The 1H NMR of the title product in d6DMSO (delta) showed signals at 5.1 (m, 1H, CH(CH3)2); and 1.4 (d, 6H, CH(CH3)2).

Workup

  1. customThe resulting solution (which contained 91% 2,3,5-tribromo-6-isopropoxy benzoquinone as judged by HPLC) was recrystallised from 60-80 petrol ether (136 ml)
  2. customto yield a homogeneous crystalline product (6 parts)

Sources & evidence

ORD record
ord-07365b69561647e1b92e72247eeef65e
Source dataset
uspto-grants-1994_02
Patent number
US05283355

Reaction notes

Loading…