Hydrochloric Acid → 5,6-Dihydroxy-3,4-dihydronaphthalen-1(2H)-one

HRID 847263Notes

Reaction equation

HRID 847263 reaction equation
C[O:2][C:3]1[C:12]([O:13]C)=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:15].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1(C)C=CC=CC=1>[OH:2][C:3]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 82192465,6-dimethoxy-1-tetralone

Product 1

HCID 123536405,6-Dihydroxy-3,4-dihydronaphthalen-1(2H)-oneYield 95.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution 5,6-dimethoxy-1-tetralone (100 g) in toluene (958 ml) was added aluminum chloride (200 g) in small portions. After the addition was complete the reaction was heated to 80° C. and mechanically stirred for 2 hours. The reaction was cooled and slowly poured into ice and concentrated HCl. The resulting solids were filtered and washed with cold dilute HCl. The resulting solids were taken up into monoglyme, dried (MgSO4), filtered, treated with charcoal, refiltered and concentrated. The residue was co-concentrated with acetonitrile to provide upon cooling 82.5 g of desired product as an off white solid, m.p. 191°-194° C.

Workup

  1. additionAfter the addition
  2. temperatureThe reaction was cooled
  3. filtrationThe resulting solids were filtered
  4. washwashed with cold dilute HCl
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. additiontreated with charcoal
  8. concentrationconcentrated
  9. customto provide

Sources & evidence

ORD record
ord-3fadfb3578d446d3849488a2cac1e761
Source dataset
uspto-grants-1992_08
Patent number
US05140040

Reaction notes

Loading…