Malonic Acid → 3-(Naphthalen-2-yl)acrylic acid

HRID 345773Notes

Reaction equation

HRID 345773 reaction equation
N1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7](O)(=O)[CH2:8][C:9]([OH:11])=[O:10].S(=O)(=O)(O)O>N1C=CC=CC=1>[CH:2]1[C:6]2[C:6](=[CH:2][CH:3]=[CH:4][CH:5]=2)[CH:5]=[CH:4][C:3]=1[CH:7]=[CH:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 1118Sulfuric AcidHCID 8082Piperidine

Product 1

HCID 6077373-(Naphthalen-2-yl)acrylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-naphthylaldehyde (3 g), piperidine (0.49 ml) and malonic acid (4.0 g) in pyridine (15 ml) was stirred for 2 hrs at 120° C. After cooling, the solution was acidified with conc. sulphuric acid. The solution was extracted with EtOAc. The oily layer was washed, dried, and evaporated to give the title compound (3.6 g) having the following physical data:

Workup

  1. temperatureAfter cooling
  2. extractionThe solution was extracted with EtOAc
  3. washThe oily layer was washed
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-dfb0ccdd0fcf47bc92703a14caceabf3
Source dataset
uspto-grants-1991_10
Patent number
US05059607

Reaction notes

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