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

HRID 652670Notes

Reaction equation

HRID 652670 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

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 6N 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 6N 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°.

Workup

  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

Sources & evidence

ORD record
ord-75f9cd90bd724c6db16c2735375c1c4e
Source dataset
uspto-grants-1987_06
Patent number
US04672138

Reaction notes

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