2-benzoyloxymethylene-6-methoxy-1-Tetralone → 6-Methoxy-2-methyl-1-tetralone

HRID 487665Notes

Reaction equation

HRID 487665 reaction equation
C(O[CH:10]=[C:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=2)[C:12]1=[O:23])(=O)C1C=CC=CC=1.[H][H]>C(O)(C)C.[Pt]=O>[CH3:10][CH:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=2)[C:12]1=[O:23]

Participants

5

Reactant 2

HCID 538779652-benzoyloxymethylene-6-methoxy-1-TetraloneHCID 178418361HCID 178418361, compound

Product 1

HCID 111168446-Methoxy-2-methyl-1-tetraloneYield 73.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 3776IsopropanolSolvent

Procedure

2-Benzoyloxymethylene-6-methoxy-1-tetralone (4.6 g, 0.015 mole) was hydrogenated over platinum oxide (160 mg) in isopropyl alcohol (150 mL) at 55 psi in a Parr hydrogenation apparatus. After about 90 minutes hydrogen uptake ceased and the reaction was stopped. The catalyst was removed by filtration and the solvents were removed in vacuo. The title compound (2.0 g, 0.011 mole, 70% yield) was obtained after purification by flash chromatography [gradient 10:1 to 5:1 EtOAc:Hexanes].

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-e893169f9b76468586780a54dde6d399
Source dataset
uspto-grants-1994_03
Patent number
US05296508

Reaction notes

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