Water → 4-Carboxymethoxy-3-ethoxyphenylboronic acid

HRID 30752Notes

Reaction equation

HRID 30752 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6]1[CH:18]=[C:17]([B:19]2[O:23]C(C)(C)C(C)(C)[O:20]2)[CH:16]=[CH:15][C:7]=1[O:8][CH2:9][C:10]([O:12]CC)=[O:11])[CH3:4].O.C(OCC)(=O)C>C(O)C>[C:10]([CH2:9][O:8][C:7]1[CH:15]=[CH:16][C:17]([B:19]([OH:23])[OH:20])=[CH:18][C:6]=1[O:5][CH2:3][CH3:4])([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 86605505HCID 86605505, compound

Product 1

HCID 231342404-Carboxymethoxy-3-ethoxyphenylboronic acidYield 64.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A 2 mol/L aqueous solution of sodium hydroxide (2.14 mL) was added to a solution of ethyl [2-ethoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]acetate (0.15 g) in ethanol (10 mL), and the resulting mixture was stirred at 60° C. for 3 hrs. Water and ethyl acetate were added to the reaction mixture. The aqueous layer was separated, washed with ethyl acetate, made acidic with the addition of 2 mol/L hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford the title compound (0.066 g).

Workup

  1. customThe aqueous layer was separated
  2. washwashed with ethyl acetate
  3. additionmade acidic with the addition of 2 mol/L hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9432fbf6457d43c09a8ad818b559f197
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Reaction notes

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