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Methanol → (6-((2,4-Dichlorobenzyl)oxy)-1,1-dioxido-1-benzothiophen-3-yl)acetic acid

HRID 591474
Notes
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Reaction equation

HRID 591474 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[CH:14][C:9]=2[S:8](=[O:26])(=[O:25])[CH:7]=1)C.C1COCC1.CO.O.[OH-].[Li+]>O>[Cl:24][C:18]1[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=1[CH2:16][O:15][C:13]1[CH:12]=[CH:11][C:10]2[C:6]([CH2:5][C:4]([OH:27])=[O:3])=[CH:7][S:8](=[O:26])(=[O:25])[C:9]=2[CH:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 71721636Ethyl(6-((2,4-dichlorobenzyl)oxy)-1,1-dioxido-1-benzothiophen-3-yl)acetate

Product 1

HCID 71721637(6-((2,4-Dichlorobenzyl)oxy)-1,1-dioxido-1-benzothiophen-3-yl)acetic acidYield 53.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of ethyl(6-((2,4-dichlorobenzyl)oxy)-1,1-dioxido-1-benzothiophen-3-yl)acetate (8.00 g), THF (64 mL), MeOH (64 mL) and H2O (32 mL) was added lithium hydroxide hydrate (1.58 g) and the resulting mixture was stirred at 25° C. for 16 h. The solvent was removed under reduced pressure. The residue was suspended in water, and the mixture was acidified by 6N HCl. The resulting solid was collected by filtration, and dried under reduced pressure to give the title compound (4.00 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationThe resulting solid was collected by filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-cd8669838b1341c8aef62b44d3132c90
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09238639B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes