Benzene → 2-Propenoic acid, 3-phenyl-, 2-naphthalenyl ester

HRID 247365Notes

Reaction equation

HRID 247365 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[OH-].[Na+].[C:14](Cl)(=[O:23])[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1C=CC=CC=1>CC(C)=O.O>[C:14]([O:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)(=[O:23])[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 86632-NaphtholHCID 14798Sodium HydroxideHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 7852142-Propenoic acid, 3-phenyl-, 2-naphthalenyl esterYield 80.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

In 70 ml of acetone was dissolved 6.4 g of 2-naphthol. A 25% queous sodium hydroxide solution was added to the solution. A solution of 8.1 g of cinnamoyl chloride in 10 ml of acetone was dropwise added to the mixture over 4 minutes while stirring. After the stirring was continued for 7 minutes, benzene and water were added to the system to effect liquid separation. After the organic phase was washed with an aqueous hydrogen sodium carbonate solution, the system was dried over anhydrous potassium carbonate and the solvent was distilled off. The residue was treated with n-hexane and benzene to give crystals of the product. The product was recrystallized from a solvent mixture of n-hexane and benzene to give 9.8 g of the product.

Workup

  1. customliquid separation
  2. washAfter the organic phase was washed with an aqueous hydrogen sodium carbonate solution
  3. dry with materialthe system was dried over anhydrous potassium carbonate
  4. distillationthe solvent was distilled off
  5. additionThe residue was treated with n-hexane and benzene
  6. customto give crystals of the product
  7. customThe product was recrystallized from a solvent mixture of n-hexane and benzene

Sources & evidence

ORD record
ord-00090178383f46be8306f997803f5ef6
Source dataset
uspto-grants-1987_11
Patent number
US04707463

Reaction notes

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