2-Methoxynaphthalene → 3-Methoxyacenaphthoquinone

HRID 566975

Reaction equation

HRID 566975 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[C:13](Cl)(=[O:17])[C:14](Cl)=[O:15].C(=O)=O.C(O)CO.[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5]3[C:4]=1[C:13](=[O:17])[C:14](=[O:15])[C:6]=3[CH:7]=[CH:8][CH:9]=2

Participants

6

Reactant 4

HCID 71192-MethoxynaphthaleneHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 86601574Dry ice ethyleneglycol

Product 1

HCID 22502643-MethoxyacenaphthoquinoneYield 67.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methoxynaphthalene (5 g, 31.6 mmol) and oxalyl chloride (11 mL, 126 mmol) in 150 mL of dichloromethane was cooled to −15° C. (CO2/ethylene glycol) under nitrogen. Aluminum trichloride (10.5 g, 79 mmol) was added slowly over 30 minutes. After 3 hours, the mixture was poured onto 100 g of ice. The layers were separated, and the aqueous layer was washed with dichloromethane. The combined organic layers were washed with saturated sodium bicarbonate, water, brine and dried over magnesium sulfate. The solution was concentrated to afford 4.5 g of a solid. The solid was triturated with dichloromethane to give 1.24 g of the title compound as a solid, mp 218°-220° C.; 1H NMR (DMSO-d6): δ8.38 (d, 1H), 8.25 (d, 1H), 7.90 (d, 1H), 7.63 (m, 2H), 4.07 (s, 3H).

Workup

  1. customThe layers were separated
  2. washthe aqueous layer was washed with dichloromethane
  3. washThe combined organic layers were washed with saturated sodium bicarbonate, water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-3a13157bbb5f4060a050e2da0fa024e0
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Linked notes

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