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

HRID 1507047Notes

Reaction equation

HRID 1507047 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[H-].[Na+].Br[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 18430EpibromohydrinHCID 24758Sodium hydride

Product 1

HCID 27740493-(oxiran-2-ylmethoxy)benzaldehydeYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-hydroxybenzaldehyde (2.0 g, 16.38 mmol) in DMF (30 mL) at 0° C. was added NaH (983 mg, 24.57 mmol) in portions. After 0.5 h, a solution of 2-(bromomethyl)oxirane (2.69 mg, 19.65 mmol) in DMF (5 mL) was added and the reaction mixture was warmed to room temperature for 5 h. The mixture was concentrated, dissolved in ethyl acetate and washed with water. The organic portion was dried over sodium sulfate, filtered and concentrated. The crude product was used in the next step without further purification. (2.1 g, yield 72%) MS (ESI+) e/z: 179.1 [M+1]+.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic portion was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-be67e3b35af34312a7d58b4c3d47ee48
Source dataset
uspto-grants-2015_12
Patent number
US09221794B2

Reaction notes

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