HCID 54033015, compound → HCID 54485229, compound

HRID 1402823Notes

Reaction equation

HRID 1402823 reaction equation
[C:1]1([CH:11]([CH2:16][C:17](O)=[O:18])[CH2:12][C:13]([OH:15])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>C(Cl)(=O)C>[C:1]1([CH:11]2[CH2:16][C:17](=[O:18])[O:14][C:13](=[O:15])[CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 54033015HCID 54033015, compound2×

Product 1

HCID 54485229HCID 54485229, compound

Reagents, catalysts & solvents 1

HCID 6367Acetyl chlorideSolvent

Procedure

To a solution of commercial 1-naphthaldehyde (25 g) and ethyl acetoacetate (40.5 ml) in ethanol (30 ml) piperidine (3 ml) was added with stirring at rt. The orange coloured solution was kept at rt for a week. The viscous orange oil (the bis-adduct of acetoacetate to the aldehyde) was not further purified but used directly for the next step. The oil was added in portions to 40% NaOH (500 g) with stirring and rinsed with ethanol. The resulting orange slurry was stirred at reflux for 2 h. After cooling to rt the mixture was filtered and washed with water to give an orange coloured, partly resinous solid (sodium salt of 3-(1-naphthyl)glutaric acid). The salt was slurried in conc. HCl/water 1:1 (300 ml) and kept at rt for 3 d. The remaining solid was isolated by suction filtration and washed with water. The still wet filter cake was taken up in acetone (200 ml) and the organic layer was dried by addition of sodium sulfate. After filtration the solvent was removed by distillation and the residue (32.1 g amorphous orange solid) was triturated with ethyl acetate (40 ml) to leave a light yellowish powder (11.6 g) which was identified by NMR as the desired 3-(1-naphthyl)glutaric acid. The suspension of 3-(1-naphthyl)glutaric acid in acetyl chloride (16 ml) was heated to reflux with stirring for 1.5 h. After cooling to rt precipitation of the product is completed by addition of petrol ether (100 ml). The precipitate is isolated by suction filtration, washed with petrol ether, and dried in vacuo to provide 3-(1-naphthyl)glutaric anhydride (10.54 g) as light beige solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customprecipitation of the product
  4. additionis completed by addition of petrol ether (100 ml)
  5. customThe precipitate is isolated by suction filtration
  6. washwashed with petrol ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d04f4649daa3428d855eac0ad29e33e2
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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