Methanol → 2-Hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzoic acid

HRID 2243514Notes

Reaction equation

HRID 2243514 reaction equation
C([O:8][C:9]1[CH:24]=[C:23]([B:25]2[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]2)[CH:22]=[CH:21][C:10]=1[C:11]([O:13]CC1C=CC=CC=1)=[O:12])C1C=CC=CC=1.CO>[C].[Pd].O1CCCC1>[OH:8][C:9]1[CH:24]=[C:23]([B:25]2[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]2)[CH:22]=[CH:21][C:10]=1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 887MethanolHCID 23090759Benzyl 2-benzyloxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Product 1

HCID 231343212-Hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzoic acidYield 102.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of benzyl 2-benzyloxy-4-(4,4,5,5-tetra -methyl-1,3,2-dioxaborolan-2-yl)benzoate (0.24 g), methanol (6 mL) and tetra hydrofuran (6 mL) was added 10% palladium-carbon (0.05 g) at room temperature under an atmosphere of argon. The mixture was stirred at room temperature for 3 hrs under an atmosphere of hydrogen. The catalyst was removed by filtration, and the solvent was evaporated under reduced pressure to afford the title compound (0.146 g).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0a886c09b83f47a3be71f837b1e0028e
Source dataset
uspto-grants-2010_03
Patent number
US07674938B2

Reaction notes

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