Dimethylformamide → 4-Methoxy-8-methyl-1-naphthaldehyde

HRID 1470488Notes

Reaction equation

HRID 1470488 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([CH3:13])[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.CN([CH:17]=[O:18])C.O=P(Cl)(Cl)Cl.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([CH3:13])[CH:9]=[CH:10][CH:11]=2)[C:6]([CH:17]=[O:18])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 109759531-Methoxy-5-methylnaphthalene

Product 1

HCID 866895944-Methoxy-8-methyl-1-naphthaldehydeYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a well stirred solution of 1-methoxy-5-methylnaphthalene (above Step-3 intermediate) (7.0 g, 40.7 mmol) in toluene (8 mL) and DMF (4.7 mL, 61 mmol) at 0° C. was added, POCl3 (4.6 mL, 49.6 mmol) drop wise and the reaction mixture was stirred for 45 min at 0° C. and then refluxed for 2 h. The dark red solution was cooled to RT and poured into a mixture of ice (50 mL) and 10% aq. NaOH (100 mL) with stirring. The crude product was extracted with EtOAc (4×75 mL) and the combined organic layer was washed with 1 N HCl (3×50 mL), water (3×50 mL), brine, dried (Na2SO4) and filtered. The solvent was evaporated and the residue was washed with hexanes (2×15 mL) to afford the desired compound (6.4 g, 79%) as reddish brown solid.

Workup

  1. temperaturerefluxed for 2 h
  2. extractionThe crude product was extracted with EtOAc (4×75 mL)
  3. washthe combined organic layer was washed with 1 N HCl (3×50 mL), water (3×50 mL), brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe solvent was evaporated
  7. washthe residue was washed with hexanes (2×15 mL)

Sources & evidence

ORD record
ord-669c7abb6f67404795d869c33ccbaed5
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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