Water → 2-Ethynyl-6-methoxynaphthalene

HRID 1359239Notes

Reaction equation

HRID 1359239 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]#[C:14]C(C)(O)C)[CH:7]=[CH:6]2.[OH-].[Na+].O>C1(C)C=CC=CC=1>[C:13]([C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=1)#[CH:14]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 11042846HCID 11042846, compound

Product 1

HCID 45865222-Ethynyl-6-methoxynaphthaleneYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-(6-methoxy-2-naphthyl)-2-methyl-3-butyn-2-ol (16.9 g, 69.7 mmol), powdered sodium hydroxide (3.7 g, 93 mmol) in toluene (350 mL) was refluxed for 16 hours in a flask equipped with a Dean Stark water trap. The mixture was allowed to cool to room temperature and the solvent was evaporated. The residue was purified by flash chromatography using 2.5-3% ethyl acetate in hexane as an eluant. Drying at 68° C. for 20 minutes afforded 2-ethynyl-6-methoxynaphthalene as a light yellow solid (10.1 g, 80%), mp: 111-112° C. Mass spectrum (+EI, M+) m/z 182. 1HNMR (400 MHz, DMSO-d6): δ8.00 (s, 1H), 7.8-7.85 (m, 2H), 7.45 (dd, 1H, J=8.4 Hz and 1.6 Hz), 7.35 (d, 1H, J=2.4 Hz), 7.2 (dd, 1H, J=8.9 Hz and 2.6 Hz), 4.2 (s, 1H), and 3.9 ppm (s, 3H). Elemental Analysis for C13H10O: Calculated: C, 85.69; H, 5.53; N, 0.00. Found: C, 85.50; H, 5.22; N, 0.07.

Workup

  1. temperaturewas refluxed for 16 hours in a flask
  2. customthe solvent was evaporated
  3. customThe residue was purified by flash chromatography
  4. customDrying at 68° C. for 20 minutes

Sources & evidence

ORD record
ord-b56821c8817c42b7af7df6759074110d
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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