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

HRID 622205
ノート
印刷プレビュー

反応式

HRID 622205 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].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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

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

生成物 1

HCID 152872372-Methoxy-3,4-methylenedioxybenzylalcohol収率 44%

試薬・触媒・溶媒

2
HCID 702Ethanol溶媒HCID 887Methanol溶媒2 回

実験手順

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%.

後処理

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

出典と根拠

ORDレコード
ord-c12604e9e2044bd782f3ab14cc024fc2
出典データセット
uspto-grants-1988_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04769480

反応ノート

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