Hydrochloric Acid → 4-(Hydroxymethyl)benzeneboronic acid

HRID 400242Notes

Reaction equation

HRID 400242 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([B:11]([OH:13])[OH:12])=[CH:7][CH:6]=1)=[O:4].Cl>CO>[OH:4][CH2:3][C:5]1[CH:6]=[CH:7][C:8]([B:11]([OH:13])[OH:12])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5910734-Formylphenylboronic AcidHCID 4311764Sodium borohydride

Product 1

HCID 27347064-(Hydroxymethyl)benzeneboronic acidYield 98.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

380 mg of sodium borohydride were added to a solution of 1.5 g of (4-formylphenyl)-boronic acid in 40 ml of methanol at 0° C. under an inert atmosphere, and after stirring for 30 minutes, 200 ml of 2N hydrochloric acid were added. After evaporation under reduced pressure, the crude product was extracted with ethyl acetate and the organic phase was dried over magnesium sulfate, followed by filtration and evaporation under reduced pressure to obtain 1.5 g of the expected product with a Rf=0.15 (cyclohexane/ethyl acetate 50/50).

Workup

  1. customAfter evaporation under reduced pressure
  2. extractionthe crude product was extracted with ethyl acetate
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. filtrationfollowed by filtration and evaporation under reduced pressure

Sources & evidence

ORD record
ord-270c32d97c1e4701af84bae5455208fb
Source dataset
uspto-grants-1998_10
Patent number
US05827887

Reaction notes

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