Sodium Hydroxide → 2'-Hydroxy-2-methyl[1,1'-biphenyl]-4-carboxylic acid

HRID 219806Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of methyl 2′-hydroxy-2-methylbiphenyl-4-carboxylate (3 g; 12.38 mmol; 1 eq.) in EtOH (90 mL) at RT was treated with sodium hydroxide (7.43 mL; 5 M; 37.15 mmol; 3 eq.). The reaction mixture was stirred at 60° C. for 2 hours. The reaction mixture was concentrated to give a brown solid. It was taken up in water (250 mL) and the aqueous phase was washed twice with EtOAc. The aqueous phase was acidified with HCl cc to pH 2. Then it was concentrated and extracted with EtOAc giving the title compound as an orange oil. It was purified by flash chromatomatography eluting with EtOAc:cHex (1:1) affording the title compound as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ 12.88 (br s, 1H), 9.49 (s, 1H), 7.81-7.75 (m, 2H), 7.24-7.18 (m, 2H), 7.05-7.02 (m, 1H), 6.94-6.84 (m, 2H), 2.16 (s, 3H). LC/MS (Method B): 227.2 (M−H)−. HPLC (Method A) Rt 3.26 min (Purity: 95.1%).

Workup

concentrationThe reaction mixture was concentrated
customto give a brown solid
washthe aqueous phase was washed twice with EtOAc
concentrationThen it was concentrated
extractionextracted with EtOAc giving the title compound as an orange oil
customIt was purified by flash chromatomatography
washeluting with EtOAc:cHex (1:1)

Sources & evidence

ORD record: ord-727816a48d634bc9a7880b209fcf9691
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202865B2

Reaction notes

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