2-Naphthalenecarboxaldehyde → 2-(2-Methoxyvinyl) naphthalene

HRID 648821Notes

Reaction equation

HRID 648821 reaction equation
[Na].[Cl-].[CH3:3][O:4][CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[CH:35]=O>C(O)C>[CH3:3][O:4][CH:5]=[CH:35][C:26]1[CH:27]=[CH:28][C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:25]=1

Participants

5

Reactant 3

HCID 62012-NaphthalenecarboxaldehydeHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 5360545Sodium

Product 1

HCID 543022142-(2-Methoxyvinyl) naphthaleneYield 55.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution produced by reacting sodium (0.92 g) in dry ethanol (60 ml) was added methoxymethyltriphenylphosphonium chloride (15.2 g). After stirring at room temperature for 0.5 hours, 2-naphthaldehyde (5.5 g) was added and the mixture heated at reflux for 5 hours. The mixture was evaporated to dryness and extracted with boiling ether, cooled to precipitate triphenylphosphine oxide, filtered and evaporated. The residue in dichloromethane (5 ml) was passed through a column of alumina and eluted with hexane to give 2-(2-methoxyvinyl) naphthalene (3.6 g), nD20 1.6505, which was hydrolysed in dioxan (50 ml) containing 2N sulphuric acid (5 ml) at 70° for 5 hours. After adding water, the mixture was extracted with ether, and the extract washed, (saturated sodium chloride), dried, (sodium sulphate) and evaporated to give 2-naphthylacetaldehyde (3.25 g) nD20 1.6232.

Workup

  1. customTo the solution produced
  2. temperaturethe mixture heated
  3. temperatureat reflux for 5 hours
  4. customThe mixture was evaporated to dryness
  5. extractionextracted with boiling ether
  6. temperaturecooled
  7. customto precipitate triphenylphosphine oxide
  8. filtrationfiltered
  9. customevaporated
  10. washeluted with hexane

Sources & evidence

ORD record
ord-183d2c4e0ee04d399766161a913f446f
Source dataset
uspto-grants-1988_04
Patent number
US04736065

Reaction notes

Loading…