o-Vanillin → HCID 13400171, compound

HRID 2061356Notes

Reaction equation

HRID 2061356 reaction equation
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:18]([O:20][CH:21]([O:24][CH2:25][CH3:26])[CH2:22]Br)[CH3:19]>CN(C=O)C>[CH2:18]([O:20][CH:21]([O:24][CH2:25][CH3:26])[CH2:22][O:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[CH3:19]

Participants

5

Reactant 3

HCID 8991o-VanillinHCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 13400171HCID 13400171, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension containing 2-hydroxy-3-methoxybenzaldehyde (4.0 g, 26.3 mmol) and K2CO3 (4.36 g, 31.60 mmol) in DMF (15 mL), bromoacetaldehyde diethyl acetal (4.86 mL, 31.60 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 eluting with hexane/EtOAc (4:1) to give 28 (2.60 g, 36%). 1H NMR (500 MHz, CDCl3): δ: 10.53 (1H, s, CHO), 7.42 (1H, m, ArH), 7.14-7.12 (2H, m, ArH), 4.83 (1H, t, J=5.30 Hz, CH), 4.21 (2H, d, J=5.35 Hz, CH2), 3.90 (3H, s, OCH3), 3.74-3.71 (2H, m, CH2CH3), 3.60-3.57 (2H, m, CH2CH3), 1.22 (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. washeluting with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-480c6573d5f5496da0694ad7a673747e
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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