Ammonium Chloride → HCID 14043182, compound

HRID 1939740Notes

Reaction equation

HRID 1939740 reaction equation
[CH:1]([C:3]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]2[C:5](=[C:6]([O:17][CH3:18])[CH:7]=[CH:8][C:9]=2[O:15][CH3:16])[C:4]=1[O:19][CH3:20])=[O:2].[Cl-].[NH4+]>O1CCCC1>[OH:2][CH:1]([C:3]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]2[C:5](=[C:6]([O:17][CH3:18])[CH:7]=[CH:8][C:9]=2[O:15][CH3:16])[C:4]=1[O:19][CH3:20])[CH2:1][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 110656822-Naphthalenecarboxaldehyde, 1,4,5,8-tetramethoxy-

Product 1

HCID 14043182HCID 14043182, compoundYield 169%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.8 g (33 mmole) of magnesium and 4.47 g (33 mmole) of 1-bromobutane were added to 30 ml of dry tetrahydrofuran and the mixture was stirred for 2 hours to obtain a Grignard reagent. A solution of 3 g (10.9 mmole) of 2-formyl-1,4,5,8-tetramethoxynaphthalene dissolved in 30 ml of dry tetrahydrofuran was added dropwise to the Grignard reagent over 20 minutes through a dropping funnel. The reaction mixture was stirred at normal temperature for further one hour and then 80 ml of 10% aqueous ammonium chloride solution was added thereto. The mixture was extracted twice with dichloromethane solvent, dried over anhydrous magnesium sulfate and filtered through a filter paper. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (silica gel 4.0×20 cm) using the solvent condition which increases the amount of ethylacetate so that the n-hexane/ethylacetate ratio can vary from 10:1 to 1:1, to obtain 3.08 g of the title compound as a yellow precipitate.

Workup

  1. extractionThe mixture was extracted twice with dichloromethane solvent
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered through a filter paper
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (silica gel 4.0×20 cm)
  6. temperatureincreases the amount of ethylacetate so that the n-hexane/ethylacetate ratio

Sources & evidence

ORD record
ord-d0f9d3be718b4bfe8c18ba8781df5bd5
Source dataset
uspto-grants-1997_12
Patent number
US05696276

Reaction notes

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