4-Hydroxybenzaldehyde → 4-(2-Bromoethoxy)Benzaldehyde

HRID 592087Notes

Reaction equation

HRID 592087 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Br:10][CH:11](Br)[CH3:12].O>[OH-].[Na+]>[Br:10][CH2:11][CH2:12][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 112011,1-Dibromoethane

Product 1

HCID 2627064-(2-Bromoethoxy)BenzaldehydeYield 19%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

4-hydroxy benzaldehyde (700 mg, 5.7 mmol) and dibromoethane (1.2 ml, 0.46 mmol) were taken in 10% NaOH solution (0.7 ml) and TBAS (2.5 g, 13.7 mmol) and heated at 70° C. for 16 h when TLC indicated completion of reaction. The reaction mixture was cooled to rt and poured into water and extracted with ethyl acetate. The combined organic extracts was washed with water, dried and purified by column chromatography using silica gel (100-200 mesh) to afford the pure product as colorless oil in 19% yield.

Workup

  1. customcompletion of reaction
  2. temperatureThe reaction mixture was cooled to rt
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts was washed with water
  5. customdried
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-a0b9e414e33942609835f0d004f60517
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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