1,4-Dioxane → Phenanthrene-2-carboxylic acid

HRID 895375Notes

Reaction equation

HRID 895375 reaction equation
Br[O-:2].[Na+].C([C:7]1[CH:20]=[CH:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]=2[CH:8]=1)(=O)C.[O:21]1[CH2:26]COCC1>>[C:26]([C:7]1[CH:20]=[CH:19][C:18]2[C:13]3[C:12](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11]=[CH:10][C:9]=2[CH:8]=1)([OH:21])=[O:2]

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 80060Methyl 2-phenanthryl ketoneHCID 23673712Sodium hypobromite

Product 1

HCID 13234903Phenanthrene-2-carboxylic acidYield 99.2%

Procedure

Bromine (4.7 ml, 0.091 mol) was added to an ice-cold solution of sodium hydroxide (12.7 g, 0.318 mol) in water (70 ml) to form a basic solution of sodium hypobromite. The sodium hypobromite solution was added to a stirred solution of 2-acetylphenanthrene in dioxane (70 ml) at 60-65 ° C. for 15 min. Excess sodium hypobromite was removed by the addition of 10% solution of sodium metabisulphite (20 ml). Water (300 ml) was added and approximately 100 ml of solvent was removed under reduced pressure. The reaction mixture was acidified with concentrated HCl. The precipitate formed was filtered and washed with water to give the title compound as a solid (4.01 g, 99.2%).

Workup

  1. customExcess sodium hypobromite was removed by the addition of 10% solution of sodium metabisulphite (20 ml)
  2. additionWater (300 ml) was added
  3. customapproximately 100 ml of solvent was removed under reduced pressure
  4. customThe precipitate formed
  5. filtrationwas filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-f0f617a3bb174b52a4f0a992b1192dcf
Source dataset
uspto-grants-2005_07
Patent number
US06916816B2

Reaction notes

Loading…