Acetic Acid → 6-Methoxy-2-naphthaldehyde

HRID 1075713Notes

Reaction equation

HRID 1075713 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1.[Mg].II.[C:17](O)(=[O:19])C>O1CCCC1.CN(C=O)C>[CH3:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([CH:17]=[O:19])[CH:11]=[CH:10]2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 807IodineHCID 787862-Bromo-6-methoxynaphthaleneHCID 5462224Magnesium

Product 1

HCID 769916-Methoxy-2-naphthaldehyde

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a reactor equipped with a stirrer are charged 10 grams of 2-bromo-6-methoxynaphthalene prepared as in Example 7 hereof, 1.05 grams of magnesium and 35 mL of tetrahydrofuran (THF). The reaction is initiated by addition of a crystal of iodine. After one hour of heating at reflux with stirring, 10 mL of DMF mixed with 10 mL of THF is added and the mixture is again refluxed with stirring for 1.5 hours. The reaction mixture is hydrolyzed by addition of dilute acetic acid and a precipitate of crude 6-methoxy-2-naphthaldehyde is formed. The precipitate is recovered by filtration, washed with water, and purified by crystallization from methanol.

Workup

  1. customTo a reactor equipped with a stirrer
  2. additionare charged
  3. temperatureAfter one hour of heating
  4. temperatureat reflux
  5. additionis added
  6. temperaturethe mixture is again refluxed
  7. stirringwith stirring for 1.5 hours

Sources & evidence

ORD record
ord-dcdd0f716b5146b388df8cc2fe2fd992
Source dataset
uspto-grants-1999_05
Patent number
US05907069

Reaction notes

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