Hydrochloric Acid → 6-Methoxy-2-naphthaldehyde

HRID 2229254Notes

Reaction equation

HRID 2229254 reaction equation
[Li]CCCC.Br[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1.CN([CH:22]=[O:23])C.Cl>CCCCCC.C1COCC1>[CH:22]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1)=[O:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 787862-Bromo-6-methoxynaphthaleneHCID 178418339Butyllithium

Product 1

HCID 769916-Methoxy-2-naphthaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

n-BuLi in hexane (1.59M, 125 ml) was added dropwise to a solution of 2-bromo-6-methoxynaphthalene (42.27 g) in THF (600 ml) at −78° C. and was stirred at −78+ C. for 30 minutes. To the mixture was added DMF (28 ml), and the whole was allowed to warm to room temperature. The reaction mixture was acidified with HCl and extracted with ethyl acetate. The extract was dried and concentrated to give the titled compound (32.31 g) as a colorless solid.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extract was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4a1b43a030084a2b98742d0a4acc722e
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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