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

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

Reactant 3

HCID 312751,4-Dioxane

HCID 80060Methyl 2-phenanthryl ketone

HCID 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%).