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

HRID 703519Notes

Reaction equation

HRID 703519 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 (3×) 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 (3×)
  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-55a17fa363f24074ac76f249fe3f2335
Source dataset
uspto-grants-1991_01
Patent number
US04983628

Reaction notes

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