Hydroquinone → HCID 19894591, compound

HRID 892997Notes

Reaction equation

HRID 892997 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.[OH-].[K+]>C(O)C>[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 123681,6-DibromohexaneHCID 14797Potassium Hydroxide

Product 1

HCID 19894591HCID 19894591, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of hydroquinone (16.5 g), 1,6-dibromohexane (7.32 g) and ethanol (60 ml) is added dropwise over 3-5 min to a solution of potassium hydroxide (85%, 2.0 g) and ethanol (20 ml). The mixture is heated at reflux for 4 hr and then allowed to cool. Silica gel (30 g) is added to the solution and the ethanol is removed at reduced pressure. The residue is chromatographed on silica gel (200 g) and eluted with ethyl acetate/hexane (33/67) to give the title compound, m.p. 43°-45°; MS (m/e)=272, 274 (M+).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 4 hr
  3. temperatureto cool
  4. additionSilica gel (30 g) is added to the solution
  5. customthe ethanol is removed at reduced pressure
  6. customThe residue is chromatographed on silica gel (200 g)
  7. washeluted with ethyl acetate/hexane (33/67)

Sources & evidence

ORD record
ord-6678a46fd0cf4f32aaa1c4921c254559
Source dataset
uspto-grants-1992_06
Patent number
US05120843

Reaction notes

Loading…