Water → 1-(Hexyloxy)naphthalene

HRID 2092956Notes

Reaction equation

HRID 2092956 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.I[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C([O-])([O-])=O.[K+].[K+].O>C(#N)C>[CH2:13]([O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 70051-NaphtholHCID 11430Potassium CarbonateHCID 125271-Iodohexane

Product 1

HCID 30172091-(Hexyloxy)naphthaleneYield 98.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-naphthol (5 g, 34.7 mmol), iodohexane (8.82 g, 41.6 mmol) and K2CO3 (7.2 g, 50 mmol) in acetonitrile (150 ml) were refluxed overnight under N2. After being cooled to room temperature, water (10 ml) was added and acetonitrile was evaporated. Water (150 ml) and Et2O (150 ml) were added. The ethereal layer was extracted and washed with water (2×100 ml), brine (100 ml), dried over MgSO4, filtered and evaporated to dryness to afford 7.8 g (98%) of compound 2 as an orange oil after drying at 80° C. under vacuum.

Workup

  1. customacetonitrile was evaporated
  2. additionWater (150 ml) and Et2O (150 ml) were added
  3. extractionThe ethereal layer was extracted
  4. washwashed with water (2×100 ml), brine (100 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-2dceff3044464c4fad3a7f776024df2e
Source dataset
uspto-grants-2013_05
Patent number
US08440843B2

Reaction notes

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