2-Naphthalenecarboxaldehyde → HCID 66865499, compound

HRID 990906Notes

Reaction equation

HRID 990906 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, 10H), 7.62-7.48 (m, 6H), 3.07 (t, 4H), 1.85 (p, 2H); 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-970accbaa44c4664b5d0e11bc8a7c96a
Source dataset
uspto-grants-2002_10
Patent number
US06462075B1

Reaction notes

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