Hydrochloric Acid → 2-Acetyl-6-methoxynaphthalene

HRID 2229238Notes

Reaction equation

HRID 2229238 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.CON(C)[C:22](=[O:24])[CH3:23].Cl>>[CH3:18][O:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:22](=[O:24])[CH3:23])[CH:16]=[CH:15]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 787862-Bromo-6-methoxynaphthaleneHCID 537505N-Methoxy-N-methylacetamideHCID 178418339Butyllithium

Product 1

HCID 775062-Acetyl-6-methoxynaphthaleneYield 81.9%

Procedure

n-BuLi (1.6M in hexane, 73 ml) was added dropwise to a solution of 2-bromo-6-methoxynaphthalene (25.29 g) at −78° C. and the mixture was stirred for 15 minutes. A solution of N-methoxy-N-methylacetamide (11.03 g) was added to the mixture and stirred for 1 hour at −78° C. 1N-HCl was added, and the whole was extracted with ethyl acetate. The extract was concentrated and crystallized from cyclohexane to give the titled compound (17.50 g) as a colorless powder.

Workup

  1. stirringstirred for 1 hour at −78° C
  2. extractionthe whole was extracted with ethyl acetate
  3. concentrationThe extract was concentrated
  4. customcrystallized from cyclohexane

Sources & evidence

ORD record
ord-42049ebcb6664cd9af5c3f04ff32e33a
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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