Ethanol → Ethyl 3-(1-naphthyl)propanoate

HRID 440963Notes

Reaction equation

HRID 440963 reaction equation
[C:1]1([CH2:11][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.[CH2:16](O)[CH3:17]>S(=O)(=O)(O)O>[C:1]1([CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 952541-Naphthalenepropionic acid

Product 1

HCID 10966256Ethyl 3-(1-naphthyl)propanoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A stirred solution of 50 grams (0.25 mole) of 3-(naphth-1-yl) propanoic acid and 20 drops (catalyst) of concentrated sulfuric acid in 250 mL of ethanol was heated at reflux for about 24 hours. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was dissolved in diethyl ether, and the solution was washed with two 150 mL portions of an aqueous solution saturated with sodium bicarbonate and then with 150 mL of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 56.0 grams of ethyl 3-(naphth-1-yl)propanoate. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureat reflux for about 24 hours
  2. concentrationAfter this time the reaction mixture was concentrated under reduced pressure to a residue
  3. dissolutionThe residue was dissolved in diethyl ether
  4. washthe solution was washed with two 150 mL portions of an aqueous solution saturated with sodium bicarbonate
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-816b4e0b515848758026e3f5413368e2
Source dataset
uspto-grants-1996_05
Patent number
US05521192

Reaction notes

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