Hydrochloric Acid → 7-hydroxy-3,4-dihydro-2H-naphthalen-1-one

HRID 565832Notes

Reaction equation

HRID 565832 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=[O:13])=[CH:5][CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1(C)C(C)=CC=CC=1>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=[O:13])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5718187-hydroxy-3,4-dihydro-2H-naphthalen-1-oneYield 79.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In xylene (450 ml) was dissolved 7-methoxy-1-tetralone (50.0 g) under argon atmosphere. To the mixture was added aluminum chloride (75.7 g), and the mixture was refluxed for 4.5 hours. The mixture was cooled to room temperature. To the mixture was added 3N hydrochloric acid (500 ml), and the mixture was extracted with ethyl acetate. The organic layer was separated and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate) to give 7-hydroxy-1-tetralone (36.4 g) as dark green crystals.

Workup

  1. temperaturethe mixture was refluxed for 4.5 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic layer was separated
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified with column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-b6dd6b90cfe449989fb72ffd438f980b
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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