Hydrochloric Acid → 3-(5-Methoxynaphthalen-2-yl)prop-2-enoic acid

HRID 1288209Notes

Reaction equation

HRID 1288209 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([CH:13]=O)=[CH:8]2.C(O)(=O)[CH2:16][C:17]([OH:19])=[O:18].N1CCCCC1.Cl>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([CH:13]=[CH:16][C:17]([OH:19])=[O:18])=[CH:8]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic Acid2×HCID 8082PiperidineHCID 156909705-Methoxynaphthalene-2-carbaldehyde

Product 1

HCID 544606323-(5-Methoxynaphthalen-2-yl)prop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Methoxynaphthalene-2-aldehyde (0.1 mole), malonic acid (0.2 moles), and dry pyridine (175 ml) are placed in a 1 1 round-bottom flask. The malonic acid is dissolved by shaking on a steam bath and piperidine (0.5 ml) is added. The reaction is allowed to take place on the steam bath for 4 hours. After standing at room temperature overnight, the mixture is refluxed for 1 hour and cooled. The reaction mixture is poured into 250 ml of ice water and acidified with concentrated hydrochloric acid (80 ml) with stirring. The product is collected by filtration, washed with water (4 × 150 ml) and air dried to give β-(5-methoxynaphth-2-yl)propenoic acid.

Workup

  1. customfor 4 hours
  2. temperaturethe mixture is refluxed for 1 hour
  3. temperaturecooled
  4. stirringwith stirring
  5. filtrationThe product is collected by filtration
  6. washwashed with water (4 × 150 ml) and air
  7. customdried

Sources & evidence

ORD record
ord-ba87e518cc714c1d9b93209d7d9ed74e
Source dataset
uspto-grants-1976_10
Patent number
US03987116

Reaction notes

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