Naphthalene-1,4-dicarbaldehyde → HCID 22999338, compound

HRID 1166795Notes

Reaction equation

HRID 1166795 reaction equation
[CH:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]=[O:14])=[CH:5][CH:4]=1)=[O:2].[CH:15]([Mg]Cl)([CH3:17])[CH3:16]>C1COCC1>[CH:13]([C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([CH:1]([OH:2])[CH:15]([CH3:17])[CH3:16])=[CH:4][CH:5]=1)=[O:14]

Participants

4

Reactant 2

HCID 14079445Naphthalene-1,4-dicarbaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 22999338HCID 22999338, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1,4-diformylnaphthalene (490 mg, 2.66 mmol) in THF (12 mL) was added dropwise at 0° C. isopropyl magnesium chloride (1.3 mL of a 2 M solution in THF). The mixture was stirred at room temperature for 3 hr, diluted with satd. NH4Cl (10 mL), and extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried (MgSO4) and concentrated. Flash chromatography (silicagel, hexane:ethyl acetate, 5:1) provided the title compound (81 mg, 14%).

Workup

  1. additiondiluted with satd
  2. extractionNH4Cl (10 mL), and extracted with ethyl acetate (3×10 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cf403ce2ace24202b41d113a79ddcda8
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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