6-Methoxy-2-naphthaldehyde → 4-(6-Methoxy-2-naphthalenyl)-3-buten-2-one

HRID 1457420Notes

Reaction equation

HRID 1457420 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]([CH:13]=O)[CH:7]=[CH:6]2>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]=[CH:12][C:3](=[O:2])[CH3:4])[CH:7]=[CH:6]2

Participants

3

Reactant 1

HCID 769916-Methoxy-2-naphthaldehyde

Product 1

HCID 534099264-(6-Methoxy-2-naphthalenyl)-3-buten-2-oneYield 169%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6-Methoxy-2-naphthaldehyde (110 g, 0.591 mol), basic alumina (175 g; Aldrich Chemical Co. Inc.), and acetone (1000 mL) were added to a 2-L 3-neck flask with condenser, mechanical stirrer, and thermocouple attached. The reaction was heated to reflux for 22 hrs, filtered while still hot, and washed with hot ethyl acetate (3×100 mL). The combined organics were concentrated and then put under high vacuum for 24 hours, affording 113.0 g (85%) of 4-(6-methoxy-2-naphthyl)-but-3-en-2-one (93% GC purity). mp 114°-115.5° C.; DSC 114.5° C.; 1H NMR (300 MHz, CDCl3) δ 7.80 (s,1H), 7.72-7.55 (m,4H), 7.17-7.08 (m,2H), 6.74 (d,1H, J=10 Hz), 3.89 (s,3H), 2.38 (s,3H); 13 C NMR (75 MHz, CDCl3) δ 198.7, 159.4, 144.1, 136.3, 130.5, 130.2, 129.1, 128.0, 126.7, 124.6, 119.9, 106.5, 55.8, 27.9.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 22 hrs
  3. filtrationfiltered while still hot, and
  4. washwashed with hot ethyl acetate (3×100 mL)
  5. concentrationThe combined organics were concentrated

Sources & evidence

ORD record
ord-ac8b68f8d89945a1bcdfdbbcd756997a
Source dataset
uspto-grants-1998_12
Patent number
US05847225

Reaction notes

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