Hydrochloric Acid → 2'-Cyano-5-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-4'-methylbiphenyl-3-carboxylic acid

HRID 1845320Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH:18]2[CH2:22][O:21][C:20]([CH3:24])([CH3:23])[O:19]2)[CH:13]=[C:12]([C:25]([O:27]C)=[O:26])[CH:11]=1)#[N:2].[OH-].[Li+].Cl>O1CCCC1>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH:18]2[CH2:22][O:21][C:20]([CH3:23])([CH3:24])[O:19]2)[CH:13]=[C:12]([C:25]([OH:27])=[O:26])[CH:11]=1)#[N:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 2′-cyano-5-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-4′-methylbiphenyl-3-carboxylate (72 mg, 0.19 mmol) in tetrahydrofuran (3 mL) was added 2.5 M of aq. lithium hydroxide solution (1 mL, 2.5 mmol). The reaction mixture was stirred at 60° C. overnight. The aqueous solution was acidified with 15% HCl (aq.) to pH=5, and extracted with EtOAc. The combined organic layers were concentrated in vacuo to get the title compound.

Workup

extractionextracted with EtOAc
concentrationThe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record: ord-490ff6867f9b42358917614a7fc718a6
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Reaction notes

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