Benzyl 4-(pyridin-3-yloxy)benzoate → 4-(Pyridin-3-yloxy)benzoic acid

HRID 1610601

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:23]=[CH:22][C:11]([C:12]([O:14]CC3C=CC=CC=3)=[O:13])=[CH:10][CH:9]=2)[CH:2]=1>C(O)C.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:23]=[CH:22][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of benzyl 4-(pyridin-3-yloxy)benzoate (18.0 g, 5.90 mmol) in ethanol (300 ml) was added 10% palladium/carbon (containing water by 50%, 2.0 g), and the mixture was stirred under a hydrogen stream at 80° C. overnight. The reaction solution was filtered with celite and the filtrate was concentrated. The residue was recrystallized from ethanol-hexane to give the objective substance (11.2 g, 88%).

Workup

filtrationThe reaction solution was filtered with celite
concentrationthe filtrate was concentrated
customThe residue was recrystallized from ethanol-hexane
customto give the objective substance (11.2 g, 88%)

Sources & evidence

ORD record: ord-1296fd1aaed04fa7848a8fa4f645c4b3
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982348B2

Linked notes

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