1-Naphthaldehyde → HCID 66865140, compound

HRID 990905Notes

Reaction equation

HRID 990905 reaction equation
[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:13]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[OH-:20].[Na+]>C(O)C>[C:13]1(=[C:5]2[CH2:6][CH2:7][CH2:8][C:11](=[C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH2:2]3)[C:4]2=[O:20])[C:18]2[C:17](=[CH:10][CH:1]=[CH:2][CH:3]=2)[CH:16]=[CH:15][CH2:14]1

Participants

5

Reactant 3

HCID 61951-NaphthaldehydeHCID 7967CyclohexanoneHCID 14798Sodium Hydroxide

Product 1

HCID 66865140HCID 66865140, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(77) To a solution of the 1-naphthaldehyde (1.56 g, 10.0 mmol) and cyclohexanone (491 mg, 5.0 mmol) in 2.5 ml of ethanol was added 1.0 ml 10% 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 1.35 g (72.2%) of bright-yellow flakes: mp 211.8-213.1° C. (lit. mp 212° C., Aizenshtat, et al., J. Org. Chem., 1977, 42, 2386-2394). 1H NMR (250 MHz) δ 8.46 (s, 2H), 8.09 (m, 2H), 7.89 (t, 4H), 7.61-7.46 (m 6H), 2.82 (t, 4H), 1.71 (p, 2H); 13C NMR (62.7 MHz) 190.3, 138.5, 135.5, 133.7, 133.3, 132.2, 129.1, 128.7, 127.2, 126.6, 126.4, 125.2, 125.0, 29.0, 23.8 ppm.

Workup

  1. filtrationthe solution was filtered
  2. customThe precipitate was recrystallized from ethyl acetate
  3. customto afford 1.35 g (72.2%) of bright-yellow flakes

Sources & evidence

ORD record
ord-73a6bb3aa433499996166e9a7e00919a
Source dataset
uspto-grants-2002_10
Patent number
US06462075B1

Reaction notes

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