Methanol → 4-Methoxycarbonylphenylboronic acid

HRID 1870526Notes

Reaction equation

HRID 1870526 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([B:10]([OH:12])[OH:11])=[CH:6][CH:5]=1)([OH:3])=[O:2].S(=O)(=O)(O)O.O.[CH3:19]O>>[CH3:19][O:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]([B:10]([OH:12])[OH:11])=[CH:8][CH:9]=1)=[O:3]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 27343694-Methoxycarbonylphenylboronic acid

Procedure

A solution of 4-carboxyphenylboronic acid (2.0 g) and sulfuric acid (0.1 ml) in methanol (50 ml) was refluxed overnight. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over MgSO4. The solvent was evaporated in vacuo to give 4-methoxycarbonylphenylboronic acid (1.7 g) as colorless prisms.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-fc4a711f777642d6a38ef0744f932cd9
Source dataset
uspto-grants-2000_08
Patent number
US06096780

Reaction notes

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