3-Hydroxybenzaldehyde → 3-(oxiran-2-ylmethoxy)benzaldehyde

HRID 1399803Notes

Reaction equation

HRID 1399803 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[H-].[Na+].Cl[CH2:13][CH:14]1[CH2:16][O:15]1>CN(C=O)C>[O:15]1[CH2:16][CH:14]1[CH2:13][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 7835EpichlorohydrinHCID 24758Sodium hydride

Product 1

HCID 27740493-(oxiran-2-ylmethoxy)benzaldehydeYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-hydroxybenzaldehyde (2.0 g, 16.38 mmol) in DMF (25 mL) was added NaH (60%, 982.6 mg, 24.57 mmol) at 0° C. in portions. The mixture was stirred at this temperature for 30 minutes before a solution of 2-(chloromethyl)oxirane (2.27 g, 24.57 mmol) in DMF (5 mL) was slowly added into the reaction mixture which was then allowed to reach room temperature slowly and stirred for 16 h. The solvent was removed by concentration and the residue dissolved in ethyl acetate and washed with water. T the separated organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was then purified by column chromatography. (2.2 g, yield 75%) MS (ESI+) e/z: 179.1 [M+1]+.

Workup

  1. additionwas slowly added into the reaction mixture which
  2. customto reach room temperature
  3. customThe solvent was removed by concentration
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialT the separated organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was then purified by column chromatography

Sources & evidence

ORD record
ord-3f3842823b354d9185857afab647e5eb
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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