Ammonium Chloride → (1,4-Dimethoxynaphthalen-3-yl)methanol

HRID 1742493Notes

Reaction equation

HRID 1742493 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[C:15](OC)=[O:16].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[CH2:15][OH:16]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 3859696Methyl 1,4-dimethoxy-2-naphthoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10704023(1,4-Dimethoxynaphthalen-3-yl)methanolYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5.32 g of methyl 1,4-dimethoxy-2-naphthoate [prepared as described in step (a) above] in 15 ml of tetrahydrofuran was added dropwise to a suspension of 0.98 g of lithium aluminum hydride in 15 ml of tetrahydrofuran, whilst ice-cooling. The resulting mixture was then stirred at room temperature for 1 hour, after which 20 ml of a saturated aqueous solution of ammonium chloride was added. The precipitate which formed was filtered off, and then the product was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and then concentrated by evaporation under reduced pressure, to give 3.97 g of the title compound as a pale yellow solid, melting at 63°-66° C.

Workup

  1. temperaturecooling
  2. customThe precipitate which formed
  3. filtrationwas filtered off
  4. extractionthe product was extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-d2be234e8b2c427a8ab8dc360363acce
Source dataset
uspto-grants-1994_08
Patent number
US05338855

Reaction notes

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