Hydrochloric Acid → 2-Methoxy-3,4-methylenedioxytoluene

HRID 622206Notes

Reaction equation

HRID 622206 reaction equation
Cl.COC(OC)CNC.[CH3:10][O:11][C:12]1[C:19]2[O:20][CH2:21][O:22][C:18]=2[CH:17]=[CH:16][C:13]=1[CH:14]=O>[Pd].COC1C2OCOC=2C=CC=1C=O.C(O)C>[CH3:10][O:11][C:12]1[C:19]2[O:20][CH2:21][O:22][C:18]=2[CH:17]=[CH:16][C:13]=1[CH3:14]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 85032,2-DimethoxyethylmethylamineHCID 101979461,3-Benzodioxole-5-carboxaldehyde, 4-methoxy-

Product 1

HCID 212940062-Methoxy-3,4-methylenedioxytolueneYield 8.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 101979461,3-Benzodioxole-5-carboxaldehyde, 4-methoxy-CatalystHCID 702EthanolSolvent3×

Procedure

To 100 ml of ethanol, were charged 0.18 ml of ethanol containing 22.2 g of hydrochloric acid dissolved therein, 0.79 g of N-methylaminoacetaldehyde dimethylacetal, 1.0 g of 2-methoxy-3,4-methylenedioxybenzaldehyde, 0.12 g of 5% palladium on carbon catalyst and 10 ml of ethanol, and hydrogenation was carried out in an oil bath at 70° C. for 2 hours. The amount of hydrogen absorption was 100% 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%), 0.02 g of 2-methoxy-3,4-methylene-dioxybenzylalcohol (yield 2%), 0.076 g of 2-methoxy-3,4-methylenedioxytoluene (yield 8%) and 0.007 g of 2-methoxy-3,4-methylenedioxybenzaldehyde of the starting material (conversion rate:99%). The selectivity to the desired 2-methoxy-3,4-methylenedioxy-N-methylbenzylamino dimethylacetal was 98%.

Workup

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

Sources & evidence

ORD record
ord-4e8f471999a9498fbbf1cbdc716d1893
Source dataset
uspto-grants-1988_09
Patent number
US04769480

Reaction notes

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