2-Naphthalenecarboxaldehyde → HCID 66865499, compound

HRID 2113938Notes

Reaction equation

HRID 2113938 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.[C:13]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[OH-:20].[Na+]>C(O)C>[CH2:14]1[C:15]2[C:16](=[CH:10][CH:1]=[CH:2][CH:3]=2)[CH:17]=[CH:18][C:13]1=[C:5]1[CH2:6][CH2:7][CH2:8][C:11](=[C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:1]2)[C:4]1=[O:20]

Participants

5

Reactant 3

HCID 62012-NaphthalenecarboxaldehydeHCID 7967CyclohexanoneHCID 14798Sodium Hydroxide

Product 1

HCID 66865499HCID 66865499, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(78) To a solution of the 2-naphthaldehyde (1.56 g, 10.0 mmol) and cyclohexanone (491 mg, 5.0 mmol) in 7.5 ml of ethanol was added 5 ml 40% sodium hydroxide at 0° C. After stirring for 12 hr at room temperature, the solution was filtered. The precipitate was recrystallized from ethyl acetate to afford 1.50 g (80.6%) of bright-yellow flakes: mp 179.4-180.6° C. (lit. mp 176° C., Kabli, et al., Indian J. Chem., Sect. B, 1986, 25, 152-156). 1H NMR (250 MHz) δ 8.00-7.84 (m, 10 H), 7.62-7.48 (m, 6 H), 3.07 (t, 4 H), 1.85 (p, 2 H); 13C NMR (62.7 MHz) 190.4, 137.3, 136.5, 133.7, 133.3, 130.5, 128.5, 128.1, 127.9, 127.1, 126.6, 28.6, 23.7 ppm.

Workup

  1. filtrationthe solution was filtered
  2. customThe precipitate was recrystallized from ethyl acetate
  3. customto afford 1.50 g (80.6%) of bright-yellow flakes

Sources & evidence

ORD record
ord-bdbf6754c6f74033a44ef99f9d3a7f1d
Source dataset
uspto-grants-2008_10
Patent number
US07432303B2

Reaction notes

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