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

HRID 622203Notes

Reaction equation

HRID 622203 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:15]>[Pd].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[CH2:14][OH:15].[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 2

HCID 152872372-Methoxy-3,4-methylenedioxybenzylalcoholYield 11%HCID 212940062-Methoxy-3,4-methylenedioxytolueneYield 2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent3×

Procedure

To 100 ml of ethanol, were charged 0.9 ml of ethanol containing 22.2 g of hydrochloric acid dissolved therein, 1.98 g of N-methylaminoacetaldehyde dimethylacetal, 1.0 g of 2-methoxy-3,4-methylenedioxybenzaldehyde, 10 ml of ethanol and 0.12 g of 5% palladium on carbon catalyst and hydrogenation was carried out at room temperature. The reaction was completed in 3 hours. The amount of hydrogen absorption was 103% 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 1.29 g of 2-methoxy-3,4-methylenedioxy-N-methylbenzylamino dimethylacetal (yield 82%), 0.11 g of 2-methoxy-3,4-methylenedioxybenzylalcohol (yield 11%) and 0.02 mg of 2-methoxy-3,4-methylenedioxy toluene (yield 2%), while 2-methoxy-3,4-methylenedioxybenzaldehyde of the starting material not being recognized (conversion rate:100%). The selectivity to the desired 2-methoxy-3,4-methylenedioxy-N-methylbenzylamino dimethylacetal was 88%.

Workup

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

Sources & evidence

ORD record
ord-08b601c796a94ac780155740f55491fa
Source dataset
uspto-grants-1988_09
Patent number
US04769480

Reaction notes

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