Sulfuric Acid → Methyl 7-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate

HRID 1640113Notes

Reaction equation

HRID 1640113 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([C:14]([O:16][CH3:17])=[O:15])[C:10]2=O)=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[H][H]>[Pd].CC(O)=O.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 14722817Methyl 7-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 13058284Methyl 7-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylateYield 71%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

A slurry of methyl 7-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate (6.0 g, 26 mmol) and 10% palladium on carbon (100 mg) in AcOH (120 mL), and concentrated sulfuric acid (780 μL) was allowed to stir under 30 psi of hydrogen for 2.5 h. The reaction mixture was diluted with chloroform, and filtered through Celite. The filtrate was washed with water (5×), dried over Na2SO4 and evaporated. The residue was purified by filtration through a pad of silica, to give methyl 7-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylate as an oil (4.03 g, 71%). 1H NMR (300 MHz, CD3OD): δ 6.94 (d, 1H), 6.67-6.62 (m, 2H), 3.72 (s, 3H), 3.69 (s, 3H), 2.94-2.91 (m, 2H), 2.78-2.70 (m, 3H), and 2.18-2.09 (m, 1H), and 1.86-1.73 (m, 1H).

Workup

  1. filtrationfiltered through Celite
  2. washThe filtrate was washed with water (5×)
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. filtrationThe residue was purified by filtration through a pad of silica

Sources & evidence

ORD record
ord-0db14d2d357b47daa9112ca49aea7d90
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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