Hydrochloric Acid → NSC46721

HRID 1730689Notes

Reaction equation

HRID 1730689 reaction equation
[C:1]1(C=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:13](O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1.Cl>N1C=CC=CC=1>[C:9]1([C:14](=[CH2:13])[C:15]([OH:17])=[O:16])[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic Acid2×HCID 61951-Naphthaldehyde2×HCID 8082Piperidine

Product 1

HCID 240501NSC46721

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Naphthyl acrylic acid was prepared by reaction of 1-naphthaldehyde and malonic acid. 1-Naphthaldehyde (46.8 g.), malonic acid (60.0 g.), pyridine (120 ml.), and piperidine (3 ml.) were charged into a 500 ml. round bottom flask and refluxed on a water bath for 4 hours. The reaction solution was cooled to room temperature and poured onto a mixture of 175 ml. concentrated hydrochloric acid and 300 g. of crushed ice. A white precipitate formed and the slurry was stirred until all the ice had melted. The precipitate was separated from the slurry by filtration and washed with one portion of 10% hydrochloric acid (75 ml.) and two portions of deionized water (each 75 ml.). The 1-naphthyl acrylic acid precipitate was fully dewatered by continued application of suction on the filter, and then vacuum dried at 40°C. for 24 hours.

Workup

  1. temperatureround bottom flask and refluxed on a water bath for 4 hours
  2. additionpoured onto a mixture of 175 ml
  3. customA white precipitate formed
  4. customThe precipitate was separated from the slurry by filtration
  5. washwashed with one portion of 10% hydrochloric acid (75 ml.) and two portions of deionized water (each 75 ml
  6. customvacuum dried at 40°C. for 24 hours

Sources & evidence

ORD record
ord-f64c7bade94a4b88a0e9498741c07518
Source dataset
uspto-grants-1976_11
Patent number
US03993684

Reaction notes

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