Hydrochloric Acid → 3-(2-Chloro-benzenesulfonyl)-cyclopentanecarboxylic acid

HRID 1367474Notes

Reaction equation

HRID 1367474 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])(=[O:12])=[O:11])[CH2:6]1)=[O:4].[Li+].[OH-].Cl>CO>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[S:10]([CH:7]1[CH2:8][CH2:9][CH:5]([C:3]([OH:4])=[O:2])[CH2:6]1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 669185503-(2-Chloro-benzenesulfonyl)-cyclopentanecarboxylic acid methyl ester

Product 1

HCID 669186983-(2-Chloro-benzenesulfonyl)-cyclopentanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(2-chloro-benzenesulfonyl)-cyclopentanecarboxylic acid methyl ester (0.25 g, 1.0 eq) in methanol (8.0 mL) was treated with 1N LiOH (1.6 mL, 2.0 eq). The mixture was stirred at RT for 3 h and then acidified to pH 4 with HCl 1N. The methanol was evaporated and the residue extracted with ethyl acetate. The organic phase was dried over sodium sulfate and evaporated. The title compound was obtained as a colorless oil (0.25 g, 100%) and was used crude. MS (ESI): m/z=287.3 [M−H]−.

Workup

  1. customThe methanol was evaporated
  2. extractionthe residue extracted with ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-0566d617b2754440a6374232642a4f02
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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