Water → 3-Bromo-2,5-dimethoxybenzyl Alcohol

HRID 2393580

Reaction equation

HRID 2393580 reaction equation
[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH:5]=[O:6].O.[BH4-].[Na+].C(OCC)(=O)C>C1COCC1.CCCCCC>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH2:5][OH:6]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 9310963-Bromo-2,5-dimethoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 101927773-Bromo-2,5-dimethoxybenzyl AlcoholYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 8.27 gm (33.75 mmol) of 3-bromo-2,5-dimethoxy benzaldehyde* in 40 ml THF and 20 ml water was cooled to 10° C. and treated portionwise with 3.83 gm (101.2 mmol) NaBH4. Stirring was maintained at ambient temperature until tlc analysis (silica gel; 1:4 ethyl acetate:hexane) indicated the absence of starting aldehyde. After 30 minutes the solvent was removed in vacuo and the residue was portioned between ethyl acetate and water. After washing with brine and drying (Na2SO4), the ethyl acetate extract was concentrated in vacuo to yield 8.34 gm (99%) of a white solid, mp 59°-60° C.; tlc (cited), Rf 0.12.

Workup

  1. customAfter 30 minutes the solvent was removed in vacuo
  2. washAfter washing with brine
  3. dry with materialdrying (Na2SO4)
  4. extractionthe ethyl acetate extract
  5. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-6abe74e3c66a411596eb4c01c542510a
Source dataset
uspto-grants-1998_09
Patent number
US05807897

Linked notes

Loading…