Water → 2-(2-phenylethoxy)benzaldehyde

HRID 1821345Notes

Reaction equation

HRID 1821345 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[C:13]1([CH2:12][CH2:11][O:1][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6998SalicylaldehydeHCID 7666Phenethyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 12497062-(2-phenylethoxy)benzaldehydeYield 36%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-hydroxybenzaldehyde (0.20 mL, 1.9 mmol) in DMF (2.0 mL) was added with (2-bromoethyl)benzene (0.39 mL, 2.8 mmol) and potassium carbonate (0.78 g, 5.6 mmol), stirred at room temperature for 3.0 hours and at 80° C. for 7.5 hours. The reaction mixture was added with water and ethyl acetate to separate the mixture into organic layer and aqueous layer and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 80/20) to obtain 2-(2-phenylethyloxy)benzaldehyde (0.15 g, 36%).

Workup

  1. customto separate the mixture into organic layer and aqueous layer
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 80/20)

Sources & evidence

ORD record
ord-99bf45ac39544599a7a6aed394080eb7
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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