4-Formylphenylboronic Acid → 4-(Hydroxymethyl)benzeneboronic acid

HRID 1369187Notes

Reaction equation

HRID 1369187 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([B:9]([OH:11])[OH:10])=[CH:5][CH:4]=1)=[O:2].[H][H]>O1CCCC1.[Ni]>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([B:9]([OH:11])[OH:10])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 5910734-Formylphenylboronic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 27347064-(Hydroxymethyl)benzeneboronic acidYield 97%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

15 g (100 mmol) of 4-formylphenylboronic acid were dissolved in 200 ml of tetrahydrofuran, and 0.25 g of Raney nickel were added. A stream of hydrogen was passed through the reaction mixture for 8 hours, giving 14.8 g (97 mmol) of 4-(hydroxymethyl)phenylboronic acid.

Sources & evidence

ORD record
ord-915e88b0609048e8910484e5665ba7ab
Source dataset
uspto-grants-2003_06
Patent number
US06576789B1

Reaction notes

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