Sulfuric acid magnesium salt (1:1) → 1,4-Dimethoxy-2-naphthaldehyde

HRID 1527675Notes

Reaction equation

HRID 1527675 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][O:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([O:24][CH3:25])=[CH:16][C:15]=1[CH2:26][OH:27].[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH3:12][O:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([O:24][CH3:25])=[CH:16][C:15]=1[CH:26]=[O:27]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 10704023(1,4-Dimethoxynaphthalen-3-yl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 105848151,4-Dimethoxy-2-naphthaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Pyridinium chlorochromate (PCC, 1.04 g, 4.8 mmol) was added to a flame-dried 100 mL round bottom flask followed by dry CH2Cl2 (25.0 mL) at room temperature under Argon. Alcohol 26 (0.607 g, 2.78 mmol) was dissolved in CH2Cl2 (5.0 mL) and added slowly at room temperature. The reaction was stirred for a further 12 h at room temperature before being poured into a slurry of fluoricil, MgSO4, and CH2Cl2. After stirring the suspension was filtered through celite and condensed. The resulting solid was purified by flash column chromatography (CH2Cl2) to provide 27 (0.510 g, 2.36 mmol, 85%) as white needles. The product was also purified by recrystallization in Et2O:hexanes if no starting material was present.

Workup

  1. additionadded slowly at room temperature
  2. stirringAfter stirring the suspension
  3. filtrationwas filtered through celite and condensed
  4. customThe resulting solid was purified by flash column chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-264fe43a71be47fea1f405f0f00f036b
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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