Hydrochloric Acid → [(2-Acetyl-6,7-dichlorobenzo[b]thien-5-yl)oxy]acetic acid

HRID 370988ノート

反応式

HRID 370988 の反応式
C([O:3][C:4](=[O:21])[CH2:5][O:6][C:7]1[C:18]([Cl:19])=[C:17]([Cl:20])[C:10]2[S:11][C:12]([C:14](=[O:16])[CH3:15])=[CH:13][C:9]=2[CH:8]=1)C.[OH-].[Na+].Cl.C(OCC)C>C(O)C>[C:14]([C:12]1[S:11][C:10]2[C:17]([Cl:20])=[C:18]([Cl:19])[C:7]([O:6][CH2:5][C:4]([OH:21])=[O:3])=[CH:8][C:9]=2[CH:13]=1)(=[O:16])[CH3:15]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 53636860Ethyl[(6,7-dichloro-2-acetylbenzo[b]thien-5-yl)oxy]acetate

生成物 1

HCID 13290041[(2-Acetyl-6,7-dichlorobenzo[b]thien-5-yl)oxy]acetic acid収率 46.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To 5.1 g of ethyl[(6,7-dichloro-2-acetylbenzo[b]thien-5-yl)oxy]acetate in 200 ml of 95% ethanol is added 150 ml of a 6N sodium hydroxide solution and the mixture is refluxed at 100° for 45 mins. The solvent is removed in vacuo to give a white slurry to which is added 250 ml of a 6N hydrochloric acid and 200 ml ethyl ether. The mixture is stirred for 2 hrs, filtered and the filter cake is distributed between 6N hydrochloric acid and ethyl ether. The organic layers are separated and the aqueous layers are extracted with ethyl ether. The combined organic extracts are washed, dried over anhydrous magnesium sulfate, filtered and the solvent is evaporated to give a solid. Recrystallization from acetone-hexane gives 2.2 g of [(2-acetyl-6,7-dichlorobenzo[b]thien-5-yl)oxy]acetic acid, mp 203°-205°.

後処理

  1. temperaturethe mixture is refluxed at 100° for 45 mins
  2. customThe solvent is removed in vacuo
  3. customto give a white slurry to which
  4. filtrationfiltered
  5. customThe organic layers are separated
  6. extractionthe aqueous layers are extracted with ethyl ether
  7. washThe combined organic extracts are washed
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent is evaporated
  11. customto give a solid
  12. customRecrystallization from acetone-hexane

出典と根拠

ORDレコード
ord-4486fcdfcdcc4f4aa1030d1c5c230e87
出典データセット
uspto-grants-1985_07
特許番号
US04528399

反応ノート

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