1-Naphthaldehyde → HCID 66865140, compound

HRID 1071775Notes

Reaction equation

HRID 1071775 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, 2 H), 8.09 (m, 2 H), 7.89 (t, 4 H), 7.61-7.46 (m 6 H), 2.82 (t, 4 H), 1.71 (p, 2 H); 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-e0d3dc5e15fb41d9aff1166269665841
Source dataset
uspto-grants-2005_06
Patent number
US06906105B2

Reaction notes

Loading…