p-Toluenesulfonic acid → 2-(2-Thianthrenyl)-propionic acid

HRID 1283521

反応式

HRID 1283521 の反応式
[CH:1]1[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:15](O)([CH3:19])[C:16]([OH:18])=[O:17].C1C2SC3C(=CC=CC=3)SC=2C=CC=1.C(Cl)(C(OCC)=O)=O.[Al+3].[Cl-].[Cl-].[Cl-].C1(C(=O)C(O)=O)C2SC3C(=CC=CC=3)SC=2C=CC=1.C[Mg]I.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCCl.CCOCC.C1(C)C(C)=CC=CC=1>[CH:1]1[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:15]([CH3:19])[C:16]([OH:18])=[O:17]

参加物

11

反応物 7

HCID 6101p-Toluenesulfonic acidHCID 7109ThianthreneHCID 20884Ethoxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 215112272-(2-Thianthrenyl)-2-hydroxypropionic acidHCID 681394412-Thianthrenylglyoxylic acidHCID 178418373HCID 178418373、化合物

生成物 1

HCID 215112502-(2-Thianthrenyl)-propionic acid

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 3283Diethyl Ether溶媒HCID 7237O-Xylene溶媒

実験手順

33 g. of the ethyl ester of 2-(2-thianthrenyl)-2-hydroxypropionic acid (obtainable by reacting thianthrene with ethoxalyl chloride in 1,2-dichloroethane in the presence of AlCl3 at 10°-20° and reacting the thus-obtained ethyl ester of 2-thianthrenylglyoxylic acid (m.p. 68°-69°) with CH3MgI in ether) is dissolved in 500 ml. of xylene; 1 g. of p-toluenesulfonic acid is added thereto, and the mixture is refluxed for 31/2 hours with the use of a water trap. After cooling, the reaction mixture is washed with sodium bicarbonate solution and water, separated, dried over sodium sulfate, and evaporated. The thus-produced oily ethyl ester of 2-(2-thianthrenyl)-acrylic acid is dissolved in 270 ml. of ethanol and hydrogenated on 8 g. of 4% palladium charcoal at 50° and under 6 atmospheres until the hydrogen absorption is terminated (3 hours). The product is filtered, concentrated by evaporation, and the ethyl ester of 2-(2-thianthrenyl)-propionic acid is thus obtained, b.p. 225°-229°/0.2 mm.

後処理

  1. customat 10°-20°
  2. dissolutionis dissolved in 500 ml
  3. temperaturethe mixture is refluxed for 31/2 hours with the use of a water trap
  4. temperatureAfter cooling
  5. washthe reaction mixture is washed with sodium bicarbonate solution and water
  6. customseparated
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. dissolutionThe thus-produced oily ethyl ester of 2-(2-thianthrenyl)-acrylic acid is dissolved in 270 ml
  10. customof 4% palladium charcoal at 50° and under 6 atmospheres until the hydrogen absorption
  11. customis terminated (3 hours)
  12. filtrationThe product is filtered
  13. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-ee052834d7654bafb645a061698854b1
出典データセット
uspto-grants-1976_08
特許番号
US03975403

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