5,8-Dimethoxy-1,2,3,4-tetrahydronaphthalen-2-ol → 5,8-Dimethoxy-2-tetralone

HRID 1494390Notes

Reaction equation

HRID 1494390 reaction equation
[OH:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([O:14][CH3:15])[CH:6]=[CH:7][C:8]=2[O:12][CH3:13])[CH2:3]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:13][O:12][C:8]1[CH:7]=[CH:6][C:5]([O:14][CH3:15])=[C:4]2[C:9]=1[CH2:10][CH2:11][C:2](=[O:1])[CH2:3]2

Participants

4

Reactant 2

HCID 50733415,8-Dimethoxy-1,2,3,4-tetrahydronaphthalen-2-olHCID 178418287HCID 178418287, compound

Product 1

HCID 995955,8-Dimethoxy-2-tetraloneYield 38.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The tetrahydronaphthalene (2.1 g; 10.1 mmol) was dissolved in 20 ml of methylene chloride. The resulting solution was added to a solution of 3.27 g (15.2 mmol) of pyridinium chlorochromate in 60 ml of methylene chloride. The mixture was stirred for seven hours at room temperature and then was filtered through a bed of Celite. The filtrate was evaporated in vacuo to a dark, viscous residue. The residue was dissolved in methylene chloride and placed on a flash silica column. The column was eluted with methylene chloride, and the eluate was evaporated in vacuo to give 0.8 g (38.4%) of 5,8-dimethoxy-2-tetralone as a gold, crystalline solid.

Workup

  1. filtrationwas filtered through a bed of Celite
  2. customThe filtrate was evaporated in vacuo to a dark, viscous residue
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washThe column was eluted with methylene chloride
  5. customthe eluate was evaporated in vacuo

Sources & evidence

ORD record
ord-25d7b2490c384417a4812eb4096a531d
Source dataset
uspto-grants-1991_06
Patent number
US05026707

Reaction notes

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