2-Naphthalenecarboxaldehyde → HCID 816753, compound

HRID 2229224Notes

Reaction equation

HRID 2229224 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.C1(P(=[CH:32][C:33]([O:35][CH3:36])=[O:34])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:32]/[C:33]([O:35][CH3:36])=[O:34]

Participants

4

Reactant 2

HCID 62012-NaphthalenecarboxaldehydeHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

Product 1

HCID 816753HCID 816753, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-naphthaldehyde (6.00 g) and methyl (triphenyl-phosphoranylidene)acetate (13.0 g) in toluene (100 ml) was refluxed for 14 hours. After removal of the solvent, the residue was chromatographed on silica gel (hexane:ethyl acetate:CH2Cl2=4:1:4) followed by recrystallization from hexane-cyclohexane to give the titled compound (7.19 g) as a white solid.

Workup

  1. temperaturewas refluxed for 14 hours
  2. customAfter removal of the solvent
  3. customthe residue was chromatographed on silica gel (hexane:ethyl acetate:CH2Cl2=4:1:4)
  4. customfollowed by recrystallization from hexane-cyclohexane

Sources & evidence

ORD record
ord-a1209bc79a144a7e9225627b3f60f7cb
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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