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

HRID 622205Notes

Reaction equation

HRID 622205 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.CO>[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

8

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 44%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent2×

Procedure

To 100 ml of methanol, were charged 0.16 ml of methanol containing 25 g of hydrochloric acid dissolved therein, 0.79 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 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 and 2N NaOH aqueous solution was added thereto 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, as a product, 0.88 g of 2-methoxy-3,4-methylenedioxy-N-methylbenzylamino dimethylacetal (yield 56%) and 0.44 g of 2-methoxy-3,4-methylenedioxybenzyl alcohol (yield 44%), while 2-methoxy-3,4-methylenedioxybenzaldehyde of the starting material being not recognized (conversion rate:10%). The selectivity to the desired 2-methoxy-3,4-methylenedioxy-N-methylbenzylamino dimethylacetal was 56%.

Workup

  1. dissolutiondissolved
  2. extractionThe resulting mixture was then extracted with ethyl acetate
  3. extractionThe liquid extract

Sources & evidence

ORD record
ord-c12604e9e2044bd782f3ab14cc024fc2
Source dataset
uspto-grants-1988_09
Patent number
US04769480

Reaction notes

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