Ethanol → 2-(4-Bromo-2,6-dimethylphenoxy)ethanol

HRID 30754

Reaction equation

HRID 30754 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:16]=[C:15]([CH3:17])[C:7]([O:8][CH2:9][C:10](OCC)=[O:11])=[C:6]([CH3:18])[CH:5]=1.O1CCCC1.C(O)C>O>[Br:3][C:4]1[CH:5]=[C:6]([CH3:18])[C:7]([O:8][CH2:9][CH2:10][OH:11])=[C:15]([CH3:17])[CH:16]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 875019Ethyl (4-bromo-2,6-dimethylphenoxy)acetateHCID 4311764Sodium borohydride

Product 1

HCID 537074432-(4-Bromo-2,6-dimethylphenoxy)ethanolYield 97.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium borohydride (0.21 g) was added to a mixture of ethyl (4-bromo-2,6-dimethylphenoxy)acetate (0.78 g), tetrahydrofuran (5 mL) and ethanol (5 mL), and the mixture was stirred at room temperature for 4 hrs. The reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:ethyl acetate/n-hexane=1/2) to afford the title compound (0.65 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent:ethyl acetate/n-hexane=1/2)

Sources & evidence

ORD record
ord-63919e776b274c8f99d5d3eca09608aa
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Linked notes

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