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

HRID 30734Notes

Reaction equation

HRID 30734 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-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.24 g), methanol (6 mL) and tetrahydrofuran (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-7fec85d150c94eb0a4962a1e6e4186e3
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Reaction notes

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