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

HRID 622206노트

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HRID 622206 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>[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 101979461,3-Benzodioxole-5-carboxaldehyde, 4-methoxy-촉매HCID 702Ethanol용매3회

실험 절차

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%.

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-4e8f471999a9498fbbf1cbdc716d1893
출처 데이터셋
uspto-grants-1988_09
특허 번호
US04769480

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