Hydrochloric Acid → [[6,7-Dichloro-2-(1-hydroxypropyl)benzo[b]thien-5-yl]oxy]acetic acid

HRID 1903494ノート

反応式

HRID 1903494 の反応式
C([O:3][C:4](=[O:22])[CH2:5][O:6][C:7]1[C:19]([Cl:20])=[C:18]([Cl:21])[C:10]2[S:11][C:12]([CH:14]([OH:17])[CH2:15][CH3:16])=[CH:13][C:9]=2[CH:8]=1)C.[OH-].[Na+].Cl>C(O)C.C(OCC)C>[Cl:20][C:19]1[C:7]([O:6][CH2:5][C:4]([OH:22])=[O:3])=[CH:8][C:9]2[CH:13]=[C:12]([CH:14]([OH:17])[CH2:15][CH3:16])[S:11][C:10]=2[C:18]=1[Cl:21]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13290046Ethyl [(6,7-dichloro-2-(1-hydroxypropyl]benzo[b]thien-5-yl]oxy]acetate

生成物 1

HCID 13290047[[6,7-Dichloro-2-(1-hydroxypropyl)benzo[b]thien-5-yl]oxy]acetic acid収率 85.6%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒

実験手順

To 9.5 g of ethyl[ [6,7-dichloro-2-(1-hydroxypropyl)benzo[b]thien-5-yl]oxy]acetate in 210 ml of ethanol is added 180 ml of 6 N sodium hydroxide solution and the mixture is stirred at 100° for 30 mins. The cooled mixture is concentrated in vacuo to give a white slurry which is diluted with 400 ml of ice water and 300 ml of ethyl ether. With stirring and efficient cooling, the mixture is acidified with 6 N hydrochloric acid. The acidic mixture is extracted with ethyl ether. The ether extracts are washed, dried over anhydrous magnesium sulfate and evaporated to dryness. Recrystallization of the residue from ethyl ether and hexane gives 7.5 g of [[6,7-dichloro-2-(1-hydroxypropyl)benzo[b]thien-5-yl]oxy]acetic acid, mp 156°-158°.

後処理

  1. concentrationThe cooled mixture is concentrated in vacuo
  2. customto give a white slurry which
  3. stirringWith stirring
  4. extractionThe acidic mixture is extracted with ethyl ether
  5. washThe ether extracts are washed
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated to dryness
  8. customRecrystallization of the residue from ethyl ether and hexane

出典と根拠

ORDレコード
ord-15c09e6b0dc24061a0879d480eb20872
出典データセット
uspto-grants-1984_03
特許番号
US04436748

反応ノート

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