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

HRID 1640112Notes

Reaction equation

HRID 1640112 reaction equation
[H-].[Na+].[C:3](=[O:8])([O:6][CH3:7])OC.[CH3:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][CH2:17][C:18]2=[O:21])=[CH:13][CH:12]=1.CC(O)=O>C1COCC1.O>[CH3:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][CH:17]([C:3]([O:6][CH3:7])=[O:8])[C:18]2=[O:21])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 14722817Methyl 7-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

To a suspension of sodium hydride (60% in mineral oil, 9.99 g, 250 nmuol) in THF (100 mL), was added dimethyl carbonate (21.0 mL, 249 mmol). The mixture was heated to 65° C. and a solution of 7-methoxy-1-tetralone (20.00 g, 114 nmuol) in THF (100 mL) was added. The reaction mixture was allowed to stir vigorously at 65° C. for 2 h. After this time the reaction became very vigorous, and gas was evolved. The heating bath was removed for 10 min then heating continued for an additional 1 h. AcOH (18.00 mL, 317 mmol) was added slowly, followed by water (100 mL). The mixture was extracted with Et2O (2×) and the organic solutions were combined, washed with water and saturated NaHCO3 solution, dried over Na2SO4, filtered and evaporated. The residue was purified by filtration through a pad of silica to yield methyl 7-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate as an oil. (25.2 g, 95%). LCMS: (FA) ES+ 235.0, ES− 233.0.

Workup

  1. customThe heating bath was removed for 10 min
  2. temperaturethen heating
  3. waitcontinued for an additional 1 h
  4. extractionThe mixture was extracted with Et2O (2×)
  5. washwashed with water and saturated NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. filtrationThe residue was purified by filtration through a pad of silica

Sources & evidence

ORD record
ord-d4e9123af6a14ac2a0dcf1831764e4f4
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

Loading…