1-Naphthaldehyde → HCID 66865140, compound

HRID 2113937Notes

Reaction equation

HRID 2113937 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-f67564c819374e2bb3cc7c9a2bd1edc9
Source dataset
uspto-grants-2008_10
Patent number
US07432303B2

Reaction notes

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