Water → 1,4-Dimethoxy-3-methylnaphthalene-2-carbaldehyde

HRID 232070Notes

Reaction equation

HRID 232070 reaction equation
Br[C:2]1[C:11]([CH3:12])=[C:10]([O:13][CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[O:15][CH3:16].CCCCCC.C([Li])CCC.CN(C)[CH:30]=[O:31].O>O1CCCC1>[CH:30]([C:2]1[C:11]([CH3:12])=[C:10]([O:13][CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[O:15][CH3:16])=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 2922402-Bromo-1,4-dimethoxy-3-methylnaphthaleneHCID 178418244HCID 178418244, compound

Product 1

HCID 128475291,4-Dimethoxy-3-methylnaphthalene-2-carbaldehydeYield 48.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.0 g (17.8 mmol) of 2-bromo-1,4-dimethoxy-3-methylnaphthalene in 30 ml of tetrahydrofuran was cooled to -78° C., to which 11.2 ml (17.9 mmol) of 1.6M n-butyllithium hexane solution was added dropwise, and stirred at the same temperature for 10 minutes after completion of the addition. Then 1.3 g (17.8 mmol) of dimethylformamide was added dropwise to the reaction mixture, and stirred at room temperature for 1 hour after completion of the addition. Water was added to the reaction mixture, from which the product was extracted with ethyl acetate. The extract was washed with water, dried, and concentrated. The residue was purified with silica gel column chromatography (hexane-isopropyl ether (8:2)), and crystallized from hexane-isopropyl ether, to give 2.0 g (48.9%) of 2-formyl-1,4-dimethoxy-3-methylnaphthalene. m.p. 95°-96° C.

Workup

  1. additionwas added dropwise
  2. additionafter completion of the addition
  3. stirringstirred at room temperature for 1 hour
  4. additionafter completion of the addition
  5. extractionwas extracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified with silica gel column chromatography (hexane-isopropyl ether (8:2))
  10. customcrystallized from hexane-isopropyl ether

Sources & evidence

ORD record
ord-190d4df1609b47b6b4466bf078983a7e
Source dataset
uspto-grants-1989_07
Patent number
US04851413

Reaction notes

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