Acetone → HCID 22452643, compound

HRID 2185903Notes

Reaction equation

HRID 2185903 reaction equation
C[O:2][C:3]1[C:12](OC)=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1C=O.[C:17](=[O:20])([O-])[O-:18].[K+].[K+].[CH:23](Br)([CH3:25])[CH3:24].[CH3:27]C(C)=O>>[CH:23]([O:2][C:3]1[CH:12]=[C:11]([C:17]([O:18][CH3:27])=[O:20])[C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)([CH3:25])[CH3:24]

Participants

5

Reactant 4

HCID 180AcetoneHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 134305632,3-Dimethoxynaphthalene-1-carbaldehyde

Product 1

HCID 22452643HCID 22452643, compoundYield 53%

Procedure

A mixture of methyl 3-hydroxy-1-naphthalenecarboxylate (Example 6 subpart (b)) (0.94 g, 4.65 mmol), potassium carbonate (0.96 g, 6.98 mmol), isopropyl bromide (0.66 mL, 6.98 mmol) and acetone (46 mL) was heated at reflux for 44 h. After filtration the solvent was removed in vacuo. Column chromatography yielded the title compound as a light yellow oil (0.6 g, 53%). 1H NMR (CDCl3) δ 8.78 (m, 1H), 7.84 (d, 1H), 7.74 (m, 1H), 7.46 (m, 2H), 7.33 (d, 1H), 4.72 (m, 1H), 3.99 (s, 3H), 1.42 (s, 3H), 1.40 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 44 h
  3. filtrationAfter filtration the solvent
  4. customwas removed in vacuo

Sources & evidence

ORD record
ord-c8d36614a86e4ddba8fa224519326f0f
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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