Dimethylformamide → HCID 15401124, compound

HRID 2268699Notes

Reaction equation

HRID 2268699 reaction equation
O[C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[C:13](=[O:16])([O-])[O-].[K+].[K+].[CH2:19](Br)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].CN(C=O)C>O>[CH2:19]([O:12][C:7]1[C:6]2[C:11](=[C:2]([O:16][CH2:13][CH2:4][CH2:3][CH2:2][CH2:11][CH3:10])[CH:3]=[CH:4][CH:5]=2)[CH:10]=[CH:9][CH:8]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 67491,5-DihydroxynaphthaleneHCID 81011-BromohexaneHCID 11430Potassium Carbonate

Product 1

HCID 15401124HCID 15401124, compoundYield 163.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a 500 mL round-bottomed flask were added 1,5-dihydroxynaphthalene (15.0 g, 0.094 mol), potassium carbonate (27.2 g, 0.2 mol), n-hexylbromide (32.5 g, 0.2 mol), and 200 mL of DMF. The reaction was heated to 90° C. overnight, cooled to room temperature, and poured into 700 mL of water. The dark brown precipitate was filtered and washed with methanol. The crude product was refluxed in methanol and then filtered to give light green solid 25.2 g (80% yield). 1H NMR (CDCl3) δ (ppm): 0.92 (t, J=6.5 Hz, 6H), 1.35-1.41 (m, 8H), 1.52-1.57 (m, 4H), 1.85-1.92 (m, 4H), 4.10 (t, J=6.4 Hz, 4H), 6.81 (d, J=7.6 Hz, 2H), 7.30-7.36 (m, 2H), 7.84 (d, J=8.3 Hz); M.p. 92-93° C.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe dark brown precipitate was filtered
  3. washwashed with methanol
  4. temperatureThe crude product was refluxed in methanol
  5. filtrationfiltered

Sources & evidence

ORD record
ord-1bb3c3e23bf54564ab8343e6d634a392
Source dataset
uspto-grants-2001_12
Patent number
US06329086B1

Reaction notes

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