Reaction #710527

Reaction equation

AlCl3

Compound J

2-(1,3-benzodioxol-5-yl)-2-methyl propanal oxime

→

desired Compound

2-(3,4-dihydroxyphenyl)-2-methylpropanal oxime

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   workup.DISTILLATION20 mL of cold distilled water
2. 2
   workup.ADDITIONwas added
3. 3
   Otherto attain room temperature
4. 4
   workup.STIRRINGstirred for 12 hours at the same temperature under N2 atmosphere
5. 5
   OtherThe reaction mixture was evaporated to dryness
6. 6
   Othertriturated several times with 2:1 ethyl acetate-CH2Cl2
7. 7
   Otherevaporated to dryness
8. 8
   OtherThe crude material was purified by preparative thin-layer chromatography

Procedure

To a suspension of anhydrous AlCl3 (193 mg, 1.45 mmol) in dry CH2Cl2 (1 mL), a solution of Compound J (60 mg, 0.29 mmol) in dry CH2Cl2 (1 mL) was added drop-wise at room temperature under N2 atmosphere and stirred at the same temperature for 3 hours. The reaction mixture was cooled to 0° C., 20 mL of cold distilled water was added, the reaction mixture was allowed to attain room temperature and stirred for 12 hours at the same temperature under N2 atmosphere. The reaction mixture was evaporated to dryness and triturated several times with 2:1 ethyl acetate-CH2Cl2 and followed by 10:1 ethyl acetate-methanol. The organic solutions were combined and evaporated to dryness. The crude material was purified by preparative thin-layer chromatography using 2:1 petroleum ether-ethyl acetate to obtain the desired Compound No. 9 (30 mg, 53%) as a white foam.

Source