Water → HCID 19738626, compound

HRID 2255816Notes

Reaction equation

HRID 2255816 reaction equation
CN([CH:9]=[O:10])C1C=CC=CC=1.O=P(Cl)(Cl)Cl.[CH3:16][O:17][CH2:18][CH2:19][O:20][C:21]1[C:34]2[C:25](=[CH:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:24]=[CH:23][CH:22]=1.O>C(Cl)Cl>[CH3:16][O:17][CH2:18][CH2:19][O:20][C:21]1[C:34]2[C:25](=[CH:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:24]([CH:9]=[O:10])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 19738630HCID 19738630, compound

Product 1

HCID 19738626HCID 19738626, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 1 L 3-necked RB flask equipped with overhead stirrer, condenser, addition funnel and N2 inlet line with bubbler was added N-methylformanilide (Aldrich, 72 g, 0.53 mol, 65.75 mL) and CH2Cl2 (150 mL). After cooling to 0°, POCl3 (Aldrich, 69.0 g, 0.44 mol, 42 mL) was added dropwise (maintaining the reaction mixture at 0°) over 20 min. The solution was allowed to warm to RT and a solution of 1-[(2-methoxy)ethoxy]anthracene (1B, 60.0 g, 0.24 mol) in CH2Cl2 (200 mL) added dropwise over 10 min. The solution warmed and turned a deep red color during this addition. The reaction mixture was refluxed for 5 h, cooled and hydrolyzed by the dropwise addition of H2O (50 mL) over 1 h. The H2O was then removed and the volume of the solution reduced to 200 mL. the solution was applied to a plug of SiO2 (1 kg) and chromatographed using CH2Cl2 followed by EtOAc as the eluting solvents. The appropriate fractions were combined and the solvent removed by rotary evaporation to give a yellow oil which solidified upon cooling. Recrystallization (abs. EtOH) gave 40.87 g (60.7%) of yellow 4-[2-(methoxy)ethoxy]-1-anthracenecarbaldehyde, m.p. 72°-74°, (C,H).

Workup

  1. customTo a 1 L 3-necked RB flask equipped with overhead stirrer, condenser, addition funnel and N2 inlet line with bubbler
  2. temperatureAfter cooling to 0°
  3. temperaturemaintaining the reaction mixture at 0°) over 20 min
  4. temperatureThe solution warmed
  5. additionduring this addition
  6. temperatureThe reaction mixture was refluxed for 5 h
  7. customThe H2O was then removed
  8. customchromatographed
  9. customthe solvent removed by rotary evaporation
  10. customto give a yellow oil which
  11. temperatureupon cooling
  12. customRecrystallization (abs. EtOH)

Sources & evidence

ORD record
ord-2bbc50570016459cb118eb07cc98f974
Source dataset
uspto-grants-1993_08
Patent number
US05241107

Reaction notes

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