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

HRID 365130Notes

Reaction equation

HRID 365130 reaction equation
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1C=O.Cl>N1C=CC=CC=1>[CH:16]1[C:17]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[CH:14][C:15]=1[CH:1]=[CH:2][C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 62012-Naphthalenecarboxaldehyde

Product 1

HCID 6077373-(Naphthalen-2-yl)acrylic acidYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Malonic acid (7.5 g, 72.1 mmole) and 2-naphthaldehyde (5.0 g, 32.0 mmole) were dissolved in pyridine (20 mL) and refluxed for 1 hour. After cooling to room temperature, the reaction mixture was poured into 2N HCl solution (200 mL). The product precipitated immediately. It was collected by filtration and recrystallized from aqueous ethanol (200 mL ethanol/50 mL water) to give colorless needles (5.2 g, 82%).

Workup

  1. temperaturerefluxed for 1 hour
  2. customThe product precipitated immediately
  3. filtrationIt was collected by filtration
  4. customrecrystallized from aqueous ethanol (200 mL ethanol/50 mL water)

Sources & evidence

ORD record
ord-eb69d57ca9ee4d7fb920ca9373fbc764
Source dataset
uspto-grants-1986_08
Patent number
US04608390

Reaction notes

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