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

HRID 622202ノート

反応式

HRID 622202 の反応式
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]

参加物

7

反応物 3

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

生成物 2

HCID 152872372-Methoxy-3,4-methylenedioxybenzylalcohol収率 1%HCID 212940062-Methoxy-3,4-methylenedioxytoluene収率 0.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒3 回

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-e01060e1fb904a2ab59da512a2194dd2
出典データセット
uspto-grants-1988_09
特許番号
US04769480

反応ノート

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