Sodium Hydroxide → [(6,7-Dichloro-2-(1-hydroxy-1-methylethyl)benzo[b]thien-5-yl]oxy]acetic acid

HRID 485900Notes

Reaction equation

HRID 485900 reaction equation
[Cl:1][C:2]1[C:3]([O:16][CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])=[CH:4][C:5]2[CH:9]=[C:8]([C:10]([OH:13])([CH3:12])[CH3:11])[S:7][C:6]=2[C:14]=1[Cl:15].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[C:3]([O:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:4][C:5]2[CH:9]=[C:8]([C:10]([OH:13])([CH3:12])[CH3:11])[S:7][C:6]=2[C:14]=1[Cl:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13290043t-Butyl [[6,7-dichloro-2-(1-hydroxy-1-methylethyl)benzo[b]thien-5-yl]oxy]acetate

Product 1

HCID 13290044[(6,7-Dichloro-2-(1-hydroxy-1-methylethyl)benzo[b]thien-5-yl]oxy]acetic acidYield 93.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 8.5 g of t-butyl [[6,7-dichloro-2-(1-hydroxy-1-methylethyl)benzo[b]thien-5-yl]oxy]acetate in 200 ml of ethanol is added 150 ml of a 6N sodium hydroxide solution and the mixture is refluxed at 100° for 30 mins. The cooled mixture is concentrated in vacuo to a white slurry which is diluted with 200 ml of ice water and 200 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 and the ether extracts are washed, dried over anhydrous magnesium sulfate, filtered and the solvent is removed. Recrystallization of the residue from acetone and pentane gives 6.8 g of [[6,7-dichloro-2-(1-hydroxy-1-methylethyl)benzo[b]thien-5-yl]oxy]acetic acid, mp 194°-196°.

Workup

  1. temperaturethe mixture is refluxed at 100° for 30 mins
  2. concentrationThe cooled mixture is concentrated in vacuo to a white slurry which
  3. additionis diluted with 200 ml of ice water and 200 ml of ethyl ether
  4. extractionThe acidic mixture is extracted with ethyl ether
  5. washthe ether extracts are washed
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent is removed
  9. customRecrystallization of the residue from acetone and pentane

Sources & evidence

ORD record
ord-588553974cc141f286ec1243f7ca072f
Source dataset
uspto-grants-1985_08
Patent number
US04537976

Reaction notes

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