Water → 2-Ethenyl-6-(1-ethoxyethoxy)naphthalene

HRID 1295539Notes

Reaction equation

HRID 1295539 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH2:7]([O:9][CH:10]([O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([CH:23]=O)[CH:17]=[CH:16]2)[CH3:11])[CH3:8].O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:7]([O:9][CH:10]([O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([CH:23]=[CH2:1])[CH:17]=[CH:16]2)[CH3:11])[CH3:8]

Participants

6

Reactant 3

HCID 962WaterHCID 231357596-(1-Ethoxy ethoxy)-2-naphthaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 231357602-Ethenyl-6-(1-ethoxyethoxy)naphthaleneYield 96.3%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

In a 1 L three neck flask, equipped with an overhead mechanical stirrer, was added 45 g of methyltriphenylphosphonium bromide (0.126 mol) under nitrogen atmosphere. To this were added anhydrous 300 mL of THF and 16.02 g of potassium tert-butoxide (0.1428 mol). After 1 h of stirring, 20 g of 6-(1-ethoxy ethoxy)-2-naphthaldehyde (0.0819 mol), dissolved in 50 mL of THF, was added dropwise using a cannular and the reaction mixture was stirred overnight. After overnight stirring, deionized water (200 mL) was added with a syringe and the phases were separated. The aqueous phase was extracted with ether (2×100 mL) and the combined extracts were dried over MgSO4. After filtration and concentration, the crude product was purified by column chromatography (silica gel, hexane/CH2Cl2 40/60˜10/90) to yield 19.12 g of pure 6-(1-ethoxy ethoxy)-2-vinylnaphthalene (96%).

Workup

  1. additionwas added dropwise
  2. stirringwas stirred overnight
  3. stirringAfter overnight stirring
  4. customthe phases were separated
  5. extractionThe aqueous phase was extracted with ether (2×100 mL)
  6. dry with materialthe combined extracts were dried over MgSO4
  7. filtrationAfter filtration and concentration
  8. customthe crude product was purified by column chromatography (silica gel, hexane/CH2Cl2 40/60˜10/90)

Sources & evidence

ORD record
ord-f4da50241bf44b99991b984e1bf7525f
Source dataset
uspto-grants-2007_07
Patent number
US07244542B2

Reaction notes

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