Hydrochloric Acid → 5-(Hydroxy(phenyl)methyl)-4'-methylbiphenyl-3-carboxylic acid

HRID 1845259Notes

Reaction equation

[OH:1][CH:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:3]1[CH:4]=[C:5]([C:16]([O:18]CC)=[O:17])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:8]=1.[OH-].[Li+].Cl>O1CCOCC1.O>[OH:1][CH:2]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:3]1[CH:4]=[C:5]([C:16]([OH:18])=[O:17])[CH:6]=[C:7]([C:9]2[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=2)[CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 5-(hydroxy(phenyl)methyl)-4′-methylbiphenyl-3-carboxylate (230 mg, 0.66 mmol) in 1,4-dioxane (2 mL) and water (1 mL) was added lithium hydroxide (48 mg, 2 mmol). The reaction mixture was stirred at 60° C. overnight. After cooling, the mixture was acidified with 15% HCl (aq.) to pH=5, and extracted with EtOAc. The organic layer was dried and concentrated in vacuo to afford the title compound as a white solid. 1H NMR (300 MHz, acetone-d6): 8.14 (t, 1H, J=2.0 Hz), 8.09 (m, 1H), 7.97 (m, 1H), 7.60-7.47 (m, 4H), 7.37-7.19 (m, 5H), 6.00 (s, 1H), 2.37 (s, 3H).

Workup

temperatureAfter cooling
extractionextracted with EtOAc
customThe organic layer was dried
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ecede689ec8d4c42be95557e01f9239f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Reaction notes

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