Lithium borohydride → 2-(2,3-Dimethylphenoxy)ethanol

HRID 2175227Notes

Reaction equation

HRID 2175227 reaction equation
[CH3:1][C:2]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6](OCC)=[O:7].[BH4-].[Li+]>C1COCC1>[CH3:1][C:2]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][CH2:5][CH2:6][OH:7]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 17065225Ethyl [(2,3-dimethylphenyl)oxy]acetate

Product 1

HCID 195937292-(2,3-Dimethylphenoxy)ethanolYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(2,3-dimethylphenoxy)acetate (1.7 g, 8.16 mmol) in THF (50 mL) at 0° C. was added lithium borohydride (2 M in THF, 8.16 mL, 16.33 mmol) dropwise over a period of 10 min. At the conclusion of this period, the reaction mixture was slowly warmed to room temperature where it stirred for 16 h. After this time, the reaction mixture was quenched slowly with saturated NH4Cl, and the organic layer was separated, washed with water and brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to afford the title compound (1.06 g, 78% yield). LCMS, [M+H]+=167.0.

Workup

  1. customAfter this time, the reaction mixture was quenched slowly with saturated NH4Cl
  2. customthe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b17a3c56ef8a477eac5d4e1eee6c73a3
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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