Réaction #67913

Équation de réaction

2-allyloxymethyl-3-methoxy-benzoic acid N′-tert-butyl-hydrazide

3,5-dimethylbenzoyl chloride

K2CO3

→

3,5-dimethyl-benzoic acid N′-(2-allyloxymethyl-3-methoxy-benzoyl)-N-tert-butyl-hydrazide

Rendement 83.1%

Solvants

CH2Cl2

CH2Cl2

H2O

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONThe reaction mixture was diluted
2. 2
   Autrepartitioned
3. 3
   Autrethe organic phase was dried
4. 4
   Autresolvent was removed in vacuio
5. 5
   AutreThe product was purified by silica gel chromatography
6. 6
   Lavageeluting in 25% ethyl acetate

Mode opératoire

To a flask containing 2.0 g (0.0068 mol) of 2-allyloxymethyl-3-methoxy-benzoic acid N′-tert-butyl-hydrazide dissolved in 15 mL of CH2Cl2, was added 1.27 g (0.0075 mol) of 3,5-dimethylbenzoyl chloride in 10 mL of CH2Cl2 and 2.84 g of K2CO3 (0.02 mol) in 30 mL of H2O. The mixture was stirred at room temperature for 24 hours. The reaction mixture was diluted and partitioned, and the organic phase was dried and solvent was removed in vacuio. The product was purified by silica gel chromatography; eluting in 25% ethyl acetate:hexane fractions, to yield 2.40 g of pure 3,5-dimethyl-benzoic acid N′-(2-allyloxymethyl-3-methoxy-benzoyl)-N-tert-butyl-hydrazide. 1H NMR (CDCl3, 300 MHz) δ (ppm): 7.2 (t, 1H) 7.1 (s, 1H), 7.05 (d, 2H), 6.95 (m, 2H), 5.9 (m, 1H), 5.2-5.3 (q, 2H), 4.5 (d, 2H), 3.9 (m, 2H), 3.80 (s, 3H), 2.245 (s, 6H), 1.547 (s, 9H).

Source