Hydrochloric Acid → 4-(methylsulfonyl)-Biphenyl-2-carboxylic acid

HRID 2374239Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH:8]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:10]=1)=[O:4].[OH-].[Na+].Cl>C1COCC1>[CH3:14][S:11]([C:9]1[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH:8]=1)(=[O:12])=[O:13]

Participants

Conditions

Temperature: 60 °C

Procedure

To 4-Methanesulfonyl-biphenyl-2-carboxylic acid methyl ester (1.00 g, 3.44 mmol) in 5 ml THF was added 5 M aq NaOH solution (7.58 ml, 37.9 mmol) and the mixture was heated at 60° C. for 16 h. The mixture was then cooled to RT, acidified to pH 1 with conc hydrochloric acid, and extracted 3 times with ethyl acetate. The combined organic phases were dried with Na2SO4. Evaporation in vacuo afforded the title compound (903 mg, 95%) as an off-white crystalline solid. MS (ISN): 275.1 M−H−.

Workup

temperatureThe mixture was then cooled to RT
extractionextracted 3 times with ethyl acetate
dry with materialThe combined organic phases were dried with Na2SO4
customEvaporation in vacuo

Sources & evidence

ORD record: ord-1353a030f6f049f3b32d93de2d63a8aa
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462617B2

Reaction notes

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