Methanol → HCID 23567165, compound

HRID 235055Notes

Reaction equation

HRID 235055 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]=[C:8]2[C:13]([OH:15])=[O:14].[CH3:16]O>OS(O)(=O)=O>[CH3:16][O:14][C:13]([C:8]1[C:9]2[C:4](=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:6][CH:7]=1)=[O:15]

Participants

4

Reactant 2

HCID 887MethanolHCID 221771433,4-Dihydro-5-methoxy-1-naphthalenecarboxylic acid

Product 1

HCID 23567165HCID 23567165, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

5-Methoxy-3,4-dihydronaphthalene-1-carboxylic acid (100 g, 490 mmol) was dissolved in 800 mL of methanol and 20 mL of 96% H2SO4, and heated at reflux for hours. The reaction was then cooled and evaporated under reduced pressure to a volume of 100 mL, and quenched on ice. The aqueous mixture was extracted with diethyl ether (3×100 mL), and the organic phase was washed with water, 5% aqueous NaHCO3, brine, and then dried (MgSO4) and evaporated to yield 101 g (94%) of the title compound as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 2.36 (m, 2H), 2.78 (t, 3H), 3.83 (s, 6H), 6.82 (d, 1H), 7.14 (t, 1H), 7.19 (t, 1H), 7.40 (t, 1H).

Workup

  1. temperatureat reflux for hours
  2. temperatureThe reaction was then cooled
  3. customevaporated under reduced pressure to a volume of 100 mL
  4. customquenched on ice
  5. extractionThe aqueous mixture was extracted with diethyl ether (3×100 mL)
  6. washthe organic phase was washed with water, 5% aqueous NaHCO3, brine
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-ba3da37557c940009e7eeb56132e3fd5
Source dataset
uspto-grants-1997_01
Patent number
US05597823

Reaction notes

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