Dimethylformamide → HCID 13184845, compound

HRID 1359469Notes

Reaction equation

HRID 1359469 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8](O)=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[C:13](=[O:16])([O-])[O-].[K+].[K+].I[CH2:20][CH3:21].[CH3:22]N(C)C=O>>[CH2:20]([O:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:16][CH2:13][CH3:22])=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1)[CH3:21]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 684631,6-Naphthalenediol

Product 1

HCID 13184845HCID 13184845, compoundYield 64%

Conditions

Temperature
35 °C

Procedure

A mixture of 1,6-dihydroxynaphthalene (5.02 g, 31.3 mmole), anhydrous potassium carbonate (52.0 g, 376 mmole) , N,N-dimethylformamide (50 ml) and iodoethane (15 ml, 188 mmole) was stirred in a 35° C. oil bath for 24 hours. The reaction mixture was filtered and the solid residue was rinsed thoroughly with ethyl ether. The filtrate and the washings were combined and concentrated in vacuo to remove most of the solvents. The brown residue was partitioned between water and ether and the layers were separated. The ether layer was washed with water. The combined aqueous layers were back extracted with ether. The ether extracts were combined, washed with brine and dried over magnesium sulfate. Filtration and concentration gave a crude brown solid (6.74 g, 99% yield). Recrystallization of the crude product from hot methanol gave 1,6-diethoxynaphthalene (4.36 g, 64% yield, first crop) as a light brown solid. 1H NMR (CDCl3) δ8.20 (1H, d, phenyl), 7.06-7.36 (4H, m, phenyl), 6.66 (1H, dd, phenyl), 4.10-4.23 (4H, 2 sets of q, 2 CH2), 1.45-1.56 (6H, 2 sets if t, 2 CH3).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid residue was rinsed thoroughly with ethyl ether
  3. concentrationconcentrated in vacuo
  4. customto remove most of the solvents
  5. customThe brown residue was partitioned between water and ether
  6. customthe layers were separated
  7. washThe ether layer was washed with water
  8. extractionThe combined aqueous layers were back extracted with ether
  9. washwashed with brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationFiltration and concentration
  12. customgave a crude brown solid (6.74 g, 99% yield)
  13. customRecrystallization of the crude product from hot methanol

Sources & evidence

ORD record
ord-a9e00aa7d7ba4aee99044338658eda0e
Source dataset
uspto-grants-2003_07
Patent number
US06600015B2

Reaction notes

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