2-Naphthalenecarboxaldehyde → HCID 66865499, compound

HRID 1071776Notes

Reaction equation

HRID 1071776 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-c5d3c707e65347aea1f456068b2fe6a8
Source dataset
uspto-grants-2005_06
Patent number
US06906105B2

Reaction notes

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