4-(Dimethylamino)Benzaldehyde → HCID 54485922, compound

HRID 1703323Notes

Reaction equation

HRID 1703323 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH2:9][CH2:8][CH2:7]2)(=[O:3])[CH3:2].[CH3:14][N:15]([CH3:24])[C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.[OH-].[Na+]>C(O)C>[CH3:14][N:15]([CH3:24])[C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[CH:2][C:1]([C:4]2[CH:13]=[CH:12][C:11]3[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=3[CH:5]=2)=[O:3])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 74794-(Dimethylamino)BenzaldehydeHCID 14798Sodium HydroxideHCID 698856-Acetyltetralin

Product 1

HCID 54485922HCID 54485922, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.61 g of 6-acetyl-1,2,3,4-tetrahydronaphthalene (15 mmoles) (1), 2.23 g of p-dimethylaminobenzaldehyde (15 mmoles), and 0.66 g of sodium hydroxide in 50 ml of ethanol was stirred under nitrogen at about 60° for 90 hr. The reaction mixture was cooled in an ice bath, and the precipitated solid 3-[4-(dimethylamino)phenyl]-1-(5,6,7,8-tetrahydroaphthalen-2-yl)-2-propen-1-one was collected by filtration and washed with cold ethanol. Yield: 3.0 g (61%); m.p. 134° to 135°. λmax (CHCl3); 410 nm (ε=17,200); 266 nm (17,600). Calcd for C21C23NO: C, 82.59; H, 7.59; N, 4.59. Found: C, 80.38, 80.41; H, 7.30, 7.30; N, 3.59, 3.97.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. filtrationthe precipitated solid 3-[4-(dimethylamino)phenyl]-1-(5,6,7,8-tetrahydroaphthalen-2-yl)-2-propen-1-one was collected by filtration
  3. washwashed with cold ethanol

Sources & evidence

ORD record
ord-a022cbcc11e945c8a039e60f28be8ac4
Source dataset
uspto-grants-1982_09
Patent number
US04351893

Reaction notes

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