Ethanol → Ethyl 3-(5-methoxynaphthalen-2-yl)prop-2-enoate

HRID 1288210Notes

Reaction equation

HRID 1288210 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]=[CH:14][C:15]([OH:17])=[O:16])=[CH:8]2.S(=O)(=O)(O)O.[CH2:23](O)[CH3:24]>C(Cl)(Cl)Cl>[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:14][C:15]([O:17][CH2:23][CH3:24])=[O:16])=[CH:8]2

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 544606323-(5-Methoxynaphthalen-2-yl)prop-2-enoic acid

Product 1

HCID 53889879Ethyl 3-(5-methoxynaphthalen-2-yl)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

β-(5-methoxynaphth-2-yl)propenoic acid (0.075 moles) is allowed to reflux with 8-10 pieces of Orierite in absolute ethanol (20 ml) containing concentrated sulfuric acid (5 ml) for 21 hours. The cooled reaction mixture is diluted with chloroform and filtered hot. The filtrate is washed 3 times with water, once with 10% sodium bicarbonate and twice more with water. After drying over sodium sulfate, the solvent is removed to give ethyl β-(5-methoxynaphth-2-yl)propenoate.

Workup

  1. customThe cooled reaction mixture
  2. filtrationfiltered hot
  3. washThe filtrate is washed 3 times with water
  4. dry with materialAfter drying over sodium sulfate
  5. customthe solvent is removed

Sources & evidence

ORD record
ord-8496e4432d85419ca57085f72da427d3
Source dataset
uspto-grants-1976_10
Patent number
US03987116

Reaction notes

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