Sodium Hydroxide → 3'-(Methanesulfonyl)[1,1'-biphenyl]-4-carboxylic acid

HRID 1677147Notes

Reaction equation

HRID 1677147 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:12]=2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>CO.O1CCCC1>[CH3:20][S:17]([C:13]1[CH:12]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=2)[CH:16]=[CH:15][CH:14]=1)(=[O:18])=[O:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57980081HCID 57980081, compound

Product 1

HCID 532184333'-(Methanesulfonyl)[1,1'-biphenyl]-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Procedure HH: To a stirring solution of 3′-Methanesulfonyl-biphenyl-4-carboxylic acid methyl ester (1.0 mmol) in 1:1 methanol/tetrahydrofuran (0.15M), add 2N sodium hydroxide (3.0 mmol) and heat to reflux for 1 hour. After this time, remove the heat and concentrate in vacuo. Wash with 1N hydrochloric acid and water while extracting with 10% isopropanol/dichloromethane. Concentrate the organic layer in vacuo to yield the title compound. MS (m/e): 275.1 (M−1)

Workup

  1. temperatureheat
  2. temperatureto reflux for 1 hour
  3. customAfter this time, remove the
  4. temperatureheat
  5. concentrationconcentrate in vacuo
  6. washWash with 1N hydrochloric acid and water
  7. extractionwhile extracting with 10% isopropanol/dichloromethane
  8. concentrationConcentrate the organic layer in vacuo

Sources & evidence

ORD record
ord-7a352e07ec6d4c2680e5c0b0c7bcd79b
Source dataset
uspto-grants-2011_08
Patent number
US08008301B2

Reaction notes

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