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

HRID 622201Notes

Reaction equation

HRID 622201 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].C([BH3-])#N.[Na+].[OH-].[Na+]>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]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 85032,2-DimethoxyethylmethylamineHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 101979461,3-Benzodioxole-5-carboxaldehyde, 4-methoxy-

Product 1

HCID 152872372-Methoxy-3,4-methylenedioxybenzylalcoholYield 4.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To 100 ml of ethanol, were charged 1.83 ml of ethanol containing 22.2 g of hydrochloric acid dissolved therein, 3.96 g of N-methylaminoacetaldehyde dimethylacetal, 1.0 g of 2-methoxy-3,4-methylenedioxybenzaldehyde, 0.35 g of sodium cyanoborohydride and 10 ml of ethanol, and they were stirred in an oil bath under a nitrogen stream at 70° C. for 2 hours. After the reaction was over, the reaction mixture was cooled to room temperature, made alkaline (pH 11) with 2N NaOH solution and extracted with ethyl acetate. The liquid extract was analyzed by GC and LC to show, as a product, 1.50 g of 2-methoxy-3,4-methylenedioxy-N-methylbenzylamino dimethylacetal (yield 95%) and 0.046 g of 2-methoxy-3,4-methylenedioxy benzylalcohol (yield 4.9%), while 2-methoxy-3,4-methylenedioxy benzaldehyde of the starting material not being recognized (conversion rate:100%). The selectivity to the desired 2-methoxy-3,4-methylenedioxy-N-methylbenzylamino dimethylacetal was 95%.

Workup

  1. dissolutiondissolved
  2. extractionextracted with ethyl acetate
  3. extractionThe liquid extract

Sources & evidence

ORD record
ord-cd35ced1466c42f686cfbe4a39a0d00c
Source dataset
uspto-grants-1988_09
Patent number
US04769480

Reaction notes

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