Bromochloromethane → 7,8-Dihydro-2H-naphtho[2,3-d][1,3]dioxol-5(6H)-one

HRID 2188217Notes

Reaction equation

HRID 2188217 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[C:8](=[O:13])[CH2:7][CH2:6][CH2:5]2.[Cs].Br[CH2:16]Cl>C(#N)C>[O:1]1[C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][C:11]=2[O:12][CH2:16]1)[C:8](=[O:13])[CH2:7][CH2:6][CH2:5]3

Participants

5

Reactant 3

HCID 6333BromochloromethaneHCID 6012071(2H)-Naphthalenone, 3,4-dihydro-6,7-dihydroxy-HCID 5354618Cesium

Product 1

HCID 117693157,8-Dihydro-2H-naphtho[2,3-d][1,3]dioxol-5(6H)-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6,7-dihydroxytetralone (1 g), cesium carbonated (2.75 g), bromochloromethane (0.549 cm3) and acetonitrile (20 cm3) was heated to reflux with continual stirring for 4 h. Upon cooling, the resulting suspension was filtered through a pad of Dicalite® which was then washed further with ethyl acetate (50 cm3). The crude product was then purified by column chromatography (silica, eluting with dichloromethane) to afford the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureUpon cooling
  4. filtrationthe resulting suspension was filtered through a pad of Dicalite® which
  5. washwas then washed further with ethyl acetate (50 cm3)
  6. customThe crude product was then purified by column chromatography (silica, eluting with dichloromethane)

Sources & evidence

ORD record
ord-84ec3f0993234b7baa114fde1453b16f
Source dataset
uspto-grants-2002_06
Patent number
US06410592B1

Reaction notes

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