Potassium Carbonate → 5-Chloro-2-(2,2-diethoxyethoxy)benzaldehyde

HRID 2061359Notes

Reaction equation

HRID 2061359 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C([O-])([O-])=O.[K+].[K+].[CH2:17]([O:19][CH:20]([O:23][CH2:24][CH3:25])[CH2:21]Br)[CH3:18]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:21][CH:20]([O:23][CH2:24][CH3:25])[O:19][CH2:17][CH3:18])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 596031345-Chloro-2-(2,2-diethoxyethoxy)benzaldehydeYield 46.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 5-chloro-2-hydroxybenzaldehyde (5.0 g, 32.1 mmol) and K2CO3 (4.87 g, 35.3 mmol) in DMF (20 mL), bromoacetaldehyde diethyl acetal (5.43 mL, 35.3 mmol) was added dropwise. The mixture was refluxed for 4 h. After cooling, the precipitate was filtered off and the solvent was evaporated in vacuo. The crude residue was adsorbed on silica gel and purified by flash chromatography. The product was eluted with hexane/EtOAc (4:1) to give 33 (4.10 g, 38%) as an oil. 1H NMR (500 MHz, CDCl3): δ: 10.42 (1H, s, CHO), 7.76 (1H, d, J=2.8 Hz, ArH), 7.46 (1H, dd, J=6.15 & 2.75 Hz, ArH), 6.96 (1H, d, J=8.90 Hz, ArH), 4.87 (1H, t, J=5.25 Hz, CH), 4.10 (2H, d, J=5.25 Hz, CH2), 3.80-3.77 (2H, m, CH2CH3), 3.67-3.62 (2H, m, CH2CH3), 1.24 (6H, t, J=7.05 Hz, 2×CH3).

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was refluxed for 4 h
  3. temperatureAfter cooling
  4. filtrationthe precipitate was filtered off
  5. customthe solvent was evaporated in vacuo
  6. custompurified by flash chromatography
  7. washThe product was eluted with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-8db2b7927dc74dbebabb8dc89dcbdd70
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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