Réaction #2267068

Équation de réaction

1-(3′-methoxyphenyl)-2-propyl alcohol

1-(3-Methoxyphenyl)-2-propyl alcohol

4-nitrobenzaldehyde

→

product 3

Rendement 93.3%

3-Methyl-1-(4-nitrophenyl)-6-methoxyisochroman

Rendement 93.3%

Solvants

HCl

1,4-dioxane

Conditions de réaction

Traitement

1. 1
   TempératureThe solution was refluxed for 4 hours
2. 2
   AutreAfter removing the solvent under reduced pressure
3. 3
   Lavagethe residue was washed with cold ethanol three times

Mode opératoire

To a solution of 1-(3′-methoxyphenyl)-2-propyl alcohol 2 (0.98 g, 5.8 mmol) in 25 ml of HCl solution in 1,4-dioxane was added 4-nitrobenzaldehyde (0.91 g, 6.0 mmol) in one portion. The solution was refluxed for 4 hours. After removing the solvent under reduced pressure, the residue was washed with cold ethanol three times, affording the product 3 (1.62 g, yield 90%). 1HNMR(CDCl3): 8.20 (d, J=8.7 Hz, 2H), 7.50 (d, J=8,7 Hz, 2H), 6.65-6.48 (m, 3H), 5.78 (s, 1H), 4.01 (m, 1H), 3.76 (s, 3H), 2.80 (m, 2H), 1.40 (d, J=6.1 Hz).

Source