Methyl 5-methoxy-8-nitro-1,2,3,4-tetrahydronaphthalene-2-carboxylate → 5-Methoxy-8-nitro-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

HRID 427339Notes

Reaction equation

HRID 427339 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]([C:16]([O:18]C)=[O:17])[CH2:8]2>CO.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]([C:16]([OH:18])=[O:17])[CH2:8]2

Participants

4

Reactant 1

HCID 18622485Methyl 5-methoxy-8-nitro-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Product 1

HCID 186225095-Methoxy-8-nitro-1,2,3,4-tetrahydronaphthalene-2-carboxylic acidYield 95.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of methyl 5-methoxy-8-nitro-1,2,3,4-tetrahydronaphthalene-2-carboxylate (1.9 g, 7.1 mmol) in methanol (20 mL) and 2 M NaOH (10 mL) was refluxed for 1.5 h and the solvent was evaporated in vacuo. The residue was taken up in ethyl acetate and acidified. The organic phase was separated and dried and evaporated in vacuo to afford 1.7 g (95% yield) of crystals: mp (after recrystallization in diisopropyl ether/ethanol) 189-190° C.; EIMS (70 eV) rm/z (relative intensity) 251 (30, M+).

Workup

  1. temperaturewas refluxed for 1.5 h
  2. customthe solvent was evaporated in vacuo
  3. customThe organic phase was separated
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-abb431da227244a3b539ba935c8a2cc7
Source dataset
uspto-grants-2001_11
Patent number
US06313118B1

Reaction notes

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