2-Acetylnaphthalene → 2,2-Dihydroxy-1-(naphthalen-2-yl)ethanone

HRID 65214

Reaction equation

HRID 65214 reaction equation
C([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1)(=O)C.[Se](=O)=[O:15].[O:17]1[CH2:22][CH2:21][O:20]CC1>O>[OH:15][CH:21]([OH:20])[C:22]([C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[CH:12][CH:13]=[CH:4][CH:5]=2)[CH:10]=1)=[O:17]

Participants

5

Reactant 3

HCID 71222-AcetylnaphthaleneHCID 24007Selenium DioxideHCID 312751,4-Dioxane

Product 1

HCID 669273232,2-Dihydroxy-1-(naphthalen-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 45.1 g of 2'-acetonaphthone, 29.4 g of selenium dioxide, 350 ml of dioxane and 7.0 ml of water was stirred, heated carefully to reflux and maintained at reflux for 3 hours. The mixture was cooled, filtered through diatomaceous earth and the filtrate evaporated in vacuo. The residue was treated with 300 ml of water and the resulting white solid collected and recrystallized from aqueous acetone giving the desired product as white crystals, mp 103°-120° C.

Workup

  1. temperatureheated carefully
  2. temperatureto reflux
  3. temperaturemaintained
  4. temperatureat reflux for 3 hours
  5. temperatureThe mixture was cooled
  6. filtrationfiltered through diatomaceous earth
  7. customthe filtrate evaporated in vacuo
  8. additionThe residue was treated with 300 ml of water
  9. customthe resulting white solid collected
  10. customrecrystallized from aqueous acetone giving the desired product as white crystals, mp 103°-120° C.

Sources & evidence

ORD record
ord-bd67e94d858a409e93036f961ee4abdc
Source dataset
uspto-grants-1986_09
Patent number
US04613611

Linked notes

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