3-(5-Methoxynaphthalen-2-yl)prop-2-ynoic acid → HCID 21504103, compound

HRID 1288212Notes

Reaction equation

HRID 1288212 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]([C:13]#[C:14]C(O)=O)=[CH:8]2>N1C2C(=CC=CC=2)C=CC=1.O>[C:13]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[CH:12][C:3]=2[O:2][CH3:1])[CH:8]=1)#[CH:14]

Participants

4

Reactant 1

HCID 215040793-(5-Methoxynaphthalen-2-yl)prop-2-ynoic acid

Product 1

HCID 21504103HCID 21504103, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7047QuinolineSolvent

Procedure

5-methoxynaphth-2-ylpropiolic acid (5.85) is heated at 120-124° for 5 hours in quinoline. The reaction product is diluted with water and washed thoroughly with dilute hydrochloric acid. This is followed by washing with sodium bicarbonate (10%). The material is passed through a short aluminum (H+) column, eluted with N-hexane to give a fraction free of carbonyl absorption (I.R.). Removal of solvent gives 2-ethynyl-5-methoxynaphthalene.

Workup

  1. washwashed thoroughly with dilute hydrochloric acid
  2. washby washing with sodium bicarbonate (10%)
  3. washeluted with N-hexane
  4. customto give a fraction
  5. customfree of carbonyl absorption (I.R.)
  6. customRemoval of solvent

Sources & evidence

ORD record
ord-1fd03c315e6044288f18d467addd3acb
Source dataset
uspto-grants-1976_10
Patent number
US03987116

Reaction notes

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