Thioglycolic Acid → [{1-(6-Methyl-1,3-benzodioxol-5-yl)propyl}thio]acetic acid

HRID 486951ノート

反応式

HRID 486951 の反応式
[CH3:1][C:2]1[C:3]([CH:11](O)[CH2:12][CH3:13])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.[SH:15][CH2:16][C:17]([OH:19])=[O:18]>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][C:2]1[C:3]([CH:11]([S:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:12][CH3:13])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1

参加物

5

反応物 2

HCID 1133Thioglycolic AcidHCID 145148971-(6-Methylbenzo[d][1,3]dioxol-5-yl)propan-1-ol

生成物 1

HCID 14514911[{1-(6-Methyl-1,3-benzodioxol-5-yl)propyl}thio]acetic acid収率 90.2%

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 241Benzene溶媒

実験手順

2.27 g of 1-(6-methyl-1,3-benzodioxol-5-yl)-1-propanol, 0.1 g of p-toluenesulfonic acid and 1.52 g of mercaptoacetic acid were dissolved in 80 ml of benzene to obtain a solution. This solution was heated under reflux for 12 hours, while removing generated water. The reaction mixture was poured into water. The aqueous layer was basified and washed with ether. The aqueous layer was acidified and extracted with chloroform. The organic layer was washed with water, dried over magnesium sulfate and concentrated in a vacuum to obtain a pale yellow solid. This solid was purified by silica gel column chromatography (ethyl acetate/hexane=2:8) to obtain 2.83 g of the title compound as a white crystal.

後処理

  1. customto obtain a solution
  2. temperatureThis solution was heated
  3. temperatureunder reflux for 12 hours
  4. customwhile removing
  5. additionThe reaction mixture was poured into water
  6. washwashed with ether
  7. extractionextracted with chloroform
  8. washThe organic layer was washed with water
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in a vacuum
  11. customto obtain a pale yellow solid
  12. customThis solid was purified by silica gel column chromatography (ethyl acetate/hexane=2:8)

出典と根拠

ORDレコード
ord-75705dd5e4e64dfabc0404011fd65e95
出典データセット
uspto-grants-1994_03
特許番号
US05292901

反応ノート

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