Water → 2,6-Dihexyloxy-naphthalene

HRID 2268700Notes

Reaction equation

HRID 2268700 reaction equation
O[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[CH:3]=1.[CH2:13](Br)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:20](=[O:23])([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:13]([O:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([O:23][CH2:20][CH2:4][CH2:3][CH2:2][CH2:11][CH3:10])[CH:3]=2)[CH:8]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 935522,6-Dihydroxynaphthalene

Product 1

HCID 110565562,6-Dihexyloxy-naphthaleneYield 132.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-Dihydroxynaphthalene (30.0 g, 0.19 mol) reacted with n-hexylbromide (97.5 g, 0.59 mol) in the presence of potassium carbonate (81.6 g, 0.59 mol) in 400 mL of DMF at 90° C. overnight. The reaction was poured into 700 mL of water and the precipitate was filtered, washed with water and methanol, and dried. The crude product was recrystallized from methanol to give light gray solid 41.3 g (67% yield). 1H NMR CDCl3) δ (ppm): 0.91 (t, J=6.9 Hz, 6H), 1.32-1.40 (m, 8H), 1.44-1.54 (m, 4H), 1.77-2.86 (m, 4H), 4.02 (t, J=6.6 Hz, 4H), 7.06-7.12 (m, 4H), 7.60 (d, J=8.8 Hz, 2H); M.p. 78-79° C.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with water and methanol
  3. customdried
  4. customThe crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-cb9bf50dcda640ae93a67033b9915a88
Source dataset
uspto-grants-2001_12
Patent number
US06329086B1

Reaction notes

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