Hydrochloric Acid → 153752-69-3

HRID 487666Notes

Reaction equation

HRID 487666 reaction equation
[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12]C)[CH:8]=2)[C:3]1=[O:14].Cl.N1C=CC=CC=1.Cl>C(OCC)(=O)C>[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[C:3]1=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 111168446-Methoxy-2-methyl-1-tetralone

Product 1

HCID 4988163153752-69-3Yield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Methyl-6-Methoxy-1-Tetralone (19 g, 0.1 mole) and pyridine hydrochloride (53.1 g, 0.46 mole) were heated neet, under a nitrogen sweep at about 220° for about 2 hours. The melt was cooled, acidified with 1N HCl and dissolved in ethyl acetate. The organic layers were dried (brine, MgSO4) and concentrated in vacuo. Purification by flash chromatography [gradient 7:1 to 5:1 EtOAc:Hexanes] yielded the title compound as a light yellow solid (14.8 g, 0.084 mole, 84% yield), [Lit. Buchta et al., Ann. 576, 7-19 (1952)].

Workup

  1. temperatureThe melt was cooled
  2. dry with materialThe organic layers were dried (brine, MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography [gradient 7:1 to 5:1 EtOAc:Hexanes]

Sources & evidence

ORD record
ord-685e0475e85c4a9086f2cb08fcbb22b7
Source dataset
uspto-grants-1994_03
Patent number
US05296508

Reaction notes

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