Methyl 1,2,3,4-tetrahydro-6-methoxy-1-oxo-2-naphthaleneacetate → HCID 13934508, compound

HRID 2119235Notes

Reaction equation

HRID 2119235 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:7][CH2:6]2>Br.C(O)(=O)C>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:7][CH2:6]2

Participants

4

Reactant 1

HCID 13934507Methyl 1,2,3,4-tetrahydro-6-methoxy-1-oxo-2-naphthaleneacetate

Product 1

HCID 13934508HCID 13934508, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of the 6-methoxy-1-tetralone derivative (860 mg) (from Example 13) in 47% HBr (15 ml) and glacial acetic acid (5 ml) was refluxed for 30 hours and poured into ice-water. The product was extracted into ethyl acetate (3X) and the combined organic extracts were washed with brine, dried over Na2SO4 and concentrated to dryness. The residue was esterified with 10% HCl in methanol to give, after work-up, the title compound, m.p. 121°-123°.

Workup

  1. extractionThe product was extracted into ethyl acetate (3X)
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customto give

Sources & evidence

ORD record
ord-b73ea5104b554eb9aceaf1efa7869925
Source dataset
uspto-grants-1987_07
Patent number
US04683325

Reaction notes

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