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

HRID 622202노트

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HRID 622202 반응식
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]

참가 물질

7

반응물 3

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

생성물 2

HCID 152872372-Methoxy-3,4-methylenedioxybenzylalcohol수율 1%HCID 212940062-Methoxy-3,4-methylenedioxytoluene수율 0.8%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매3회

실험 절차

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, 10 ml of ethanol and 0.12 g of 5% palladium on carbon catalyst, and hydrogenation was carried out at room temperature for 3.5 hours. The amount of hydrogen absorption was 120% 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 1.47 g of 2-methoxy-3,4-methylenedioxy-N-methylbenzylamino dimethylacetal (yield 93%), 0.012 g of 2-methoxy-3,4-methylenedioxybenzylalcohol (yield 1%) and 7.4 mg of 2-methoxy-3,4-methylenedioxy toluene (yield 0.8%), while 2-methoxy-3,4-methylenedioxybenzaldehyde of the starting material not being recognized. The selectivity to the desired 2-methoxy-3,4-methylenedioxy-N-methylbenzylamino dimethylacetal was 99%.

후처리

  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

출처 및 근거

ORD 기록
ord-e01060e1fb904a2ab59da512a2194dd2
출처 데이터셋
uspto-grants-1988_09
특허 번호
US04769480

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