Acrolein → 2,6-Dimethylaniline

HRID 1448925ノート

反応式

HRID 1448925 の反応式
[CH:1]([CH:3]=[CH2:4])=O.[CH3:5][CH:6](N1CCOCC1)[CH:7]=[CH:8][CH3:9].[Cl-].[NH4+:17]>C(Cl)Cl>[CH3:4][C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:5])[C:1]=1[NH2:17]

参加物

5

反応物 3

HCID 7847Acrolein2 回HCID 25517Ammonium ChlorideHCID 3828336N-(3-penten-2-yl)-morpholine

生成物 1

HCID 68962,6-Dimethylaniline収率 37%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

8.4 g (0.15 mol) of acrolein is added dropwise to a solution of 23.3 g (0.15 mol) of N-(3-penten-2-yl)-morpholine in 100 ml of methylene chloride. After addition of the acrolein the mixture is stirred for 15 hours at 25° C. and subsequently for further 15 hours at 50° C. Then 12.0 g (0.225 Mol) of ammonium chloride are added and the solvent is distilled off. The residue is transferred into an autoclave and after addition of 400 ml of concentrate aqueous ammonia and 10.0 g of palladium coal (5%) the whole is heated under a nitrogen pressure of 50 bar for 15 hours at 280°-290° C. Then the catalyst is filtered off and washed with ether. The filtrate is extracted several times with ether. The extracts are combined and dried over magnesium sulphate and the ether is distilled off. The residue (14.2 g; 79% of theory) is distilled at a pressure of 15 torr. There is obtained 6.7 g (37% of theory) of 2,6-dimethylaniline, b.p. 15 : 94°-98° C.

後処理

  1. distillationthe solvent is distilled off
  2. additionafter addition of 400 ml of concentrate aqueous ammonia and 10.0 g of palladium coal (5%) the whole
  3. temperatureis heated under a nitrogen pressure of 50 bar for 15 hours at 280°-290° C
  4. filtrationThen the catalyst is filtered off
  5. washwashed with ether
  6. extractionThe filtrate is extracted several times with ether
  7. dry with materialdried over magnesium sulphate
  8. distillationthe ether is distilled off
  9. distillationThe residue (14.2 g; 79% of theory) is distilled at a pressure of 15 torr

出典と根拠

ORDレコード
ord-1b2c3d9d4d65487ba1f1c5395e4f7281
出典データセット
uspto-grants-1980_02
特許番号
US04188341

反応ノート

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