1,3-Benzodioxole-5-carboxaldehyde, 4-methoxy- → 2-Methoxy-3,4-methylenedioxybenzylalcohol

HRID 622204Notes

Reaction equation

HRID 622204 reaction equation
[CH3:1][O:2][C:3]1[C:10]2[O:11][CH2:12][O:13][C:9]=2[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6]>[Pt]>[CH3:1][O:2][C:3]1[C:10]2[O:11][CH2:12][O:13][C:9]=2[CH:8]=[CH:7][C:4]=1[CH2:5][OH:6].[CH3:1][O:2][C:3]1[C:10]2[O:11][CH2:12][O:13][C:9]=2[CH:8]=[CH:7][C:4]=1[CH3:5]

Participants

4

Reactant 1

HCID 101979461,3-Benzodioxole-5-carboxaldehyde, 4-methoxy-

Product 2

HCID 152872372-Methoxy-3,4-methylenedioxybenzylalcoholYield 13%HCID 212940062-Methoxy-3,4-methylenedioxytolueneYield 0.4%

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

The reaction was carried out in the same manner in Example 23 except for using 0.22 g of 5% platinum on carbon catalyst. The amount of hydrogen absorption was 111% of the theoretical amount. After the reaction was over, the catalyst was filtered out and 2N NaOH aqueous solution was added to the reaction mixture to make the filtrate alkaline (pH 11). The resulting mixture was then extracted with ethyl acetate. The liquid extract was analyzed by GC and LC to show 1.32 g of 2-methoxy-3,4-methylenedioxy-N-methylbenzylamino dimethylacetal (yield 84%), 0.13 g of 2-methoxy-3,4-methylenedioxybenzyl alcohol (yield 13%) and 4 mg of 2-methoxy-3,4-methylenedioxy toluene (yield 0.4%), and 0.6 mg of 2-methoxy-3,4-methylenedioxybenzaldehyde of the starting material (conversion rate:100%). The selectivity to the desired 2-methoxy-3,4-methylenedioxy-N-methylbenzylamino dimethylacetal was 87%.

Workup

  1. customThe amount of hydrogen absorption
  2. filtrationwas filtered out
  3. addition2N NaOH aqueous solution was added to the reaction mixture
  4. extractionThe resulting mixture was then extracted with ethyl acetate
  5. extractionThe liquid extract

Sources & evidence

ORD record
ord-5a9069eca5af42e8a55db57a38c8984a
Source dataset
uspto-grants-1988_09
Patent number
US04769480

Reaction notes

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