Sodium Hydroxide → 2-(4'-Chlorobiphenyl-4-ylsulfonyloxy)acetic acid

HRID 2422924Notes

Reaction equation

HRID 2422924 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([O:17][CH2:18][C:19]([O:21]CC)=[O:20])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([O:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:16])=[O:15])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86628701Ethyl 2-(4'-chlorobiphenyl-4-ylsulfonyloxy)acetate

Product 1

HCID 866287002-(4'-Chlorobiphenyl-4-ylsulfonyloxy)acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ester 12 (200 mg, 0.5633 mmol) in ethanol (0.7 ml) was treated at room temperature with 5% NaOH aqueous solution (0.45 ml). The resulting mixture was stirred at room temperature for 3 h. The ethanol was removed in vacuo and aqueous 5% HCl solution (0.46 ml) was added. The aqueous mixture was extracted with chloroform and the organic extracts dried (Na2SO4), filtered and the solvent removed under reduced pressure. The remaining white solid was recrystallized from chloroform as a white powder (133 mg, 72%). (Material that did not crystallize was collected by column chromatography using a gradient ethyl acetate to 50% MeOH in ethyl acetate). δH (400 MHz, MeOD) 4.65 (2H, s, CH2), 7.50 (2H, d, J=8.4 Hz, ArH), 7.70 (2H, d, J=8.4 Hz, ArH), 7.88 (2H, d, J=8.4 Hz, ArH), 8.02 (2H, d, J=8.4 Hz, ArH); δc (100.6 MHz, MeOD) 65.2, 127.7, 128.6, 128.8, 129.1, 134.9, 135.0, 137.7, 145.7, 168.3; MS (ES+) 343.7 (100%, [M+H2O]+), 323.7 (5%, [M+H]+), (ion not detected in ES−).

Workup

  1. customThe ethanol was removed in vacuo and aqueous 5% HCl solution (0.46 ml)
  2. additionwas added
  3. extractionThe aqueous mixture was extracted with chloroform
  4. dry with materialthe organic extracts dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe remaining white solid was recrystallized from chloroform as a white powder (133 mg, 72%)
  8. custom(Material that did not crystallize
  9. customwas collected by column chromatography

Sources & evidence

ORD record
ord-8288d24c956643b39e3765205686f514
Source dataset
uspto-grants-2011_06
Patent number
US07960434B2

Reaction notes

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