Sulfuric Acid → Sulfuric Acid

HRID 1380687ノート

反応式

HRID 1380687 の反応式
CC(C1C=CC=CC=1)C(O)=O.[CH3:12][C@@H:13]([NH:22][CH3:23])[C@@H:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.COC(C1C=CC=CC=1)C(O)=O.[S:36](=[O:40])(=[O:39])([OH:38])[OH:37].[Cl-].[Na+]>C(O)C.ClCCl.CO>[CH3:12][C@H:13]([NH:22][CH3:23])[C@H:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[S:36](=[O:38])(=[O:37])([OH:40])[OH:39]

参加物

10

反応物 5

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 9457d-Ephedrine2 回HCID 102962-Phenylpropionic acidHCID 107202Methoxyphenylacetic acid

生成物 2

HCID 1118Sulfuric AcidHCID 9294Ephedrine

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

Heat 40.0 g. (0.241 moles) of racemic (+)-α-methyl-α-phenylacetic acid [D. G. Neilson et al. J. Chem. Soc., (1962), 1519] with 40.0 g. (0.242 moles) of d-ephedrine (available from Aldrich) in 180 mL of 95% ethanol under reflux on a steam bath. Cool the resulting solution to room temperature slowly and leave undisturbed overnight (16 hrs.). Filter the resulting crystallized solid and wash same with 95% ethanol (20 mL) and ethyl ether to give 35.6 g. Recrystallize (twice) the solid from 95% ethanol to give 26.5 g. of salt of d-ephedrine and (+)-α-methoxy-α-phenylacetic acid [(+)-(S)-O-methylmandelic acid], m.p. 185°-188°, [α]D21 +72.8° (c, 4.64, MeOH). Acidify 26.3 g. of the solid with 90 mL of ice-cooled sulfuric acid, with stirring to give a solution. Add sodium chloride (31 g.) and stir the resulting mixture. Add 100 mL of dichloromethane to the mixture to give a voluminous precipitate (ephedrine, sulfuric acid salt). Add another 100 mL portion of dichloromethane to the mixture and filter the mixture through a glass filter. Wash the solid with 100 mL of dichloromethane. Shake the filtrate and separate the organic and aqueous layers. Extract the aqueous layer with 100 ml of dichloromethane. Dry the combined organic layers over anhydrous magnesium sulfate. Evaporate the solvent to give an oil which solidifies on cooling to yield 13.2 g. of the title compound as a solid: m.p. 60.5°-62.0°, [α]D22 +149° (C, 5.61, MeOH).

後処理

  1. temperatureHeat 40.0 g
  2. customleave undisturbed overnight (16 hrs.)
  3. filtrationFilter the resulting
  4. customcrystallized solid
  5. washwash same with 95% ethanol (20 mL) and ethyl ether
  6. customto give 35.6 g
  7. customRecrystallize (twice) the solid from 95% ethanol
  8. customto give 26.5 g
  9. customto give a solution

出典と根拠

ORDレコード
ord-6ebeb3f8fb1f4e4da2bd37d08701c820
出典データセット
uspto-grants-1986_04
特許番号
US04582918

反応ノート

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