Toluene → HCID 86689598, compound

HRID 1470509Notes

Reaction equation

HRID 1470509 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl.[OH-:19].[Na+].[C:21]1(C)C=CC=CC=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH:21]=[O:19])=[CH:9][CH:8]=[C:7]2[O:12][CH3:13]

Participants

6

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 123363921-Chloro-5-methoxynaphthalene

Product 1

HCID 86689598HCID 86689598, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1-chloro-5-methoxynaphthalene (step-2 intermediate) (9.2 g, 47.8 mmol) in toluene (20 mL) and DMF (5.55 mL) at 0° C. was added, POCl3 (5.4 mL, 57.3 mmol) slowly. The reaction mixture was stirred at 0° C. for 45 min and then heated to reflux for 6-8 h. The dark red solution was cooled to RT and poured into a mixture of ice (50 mL) and 10% aq. NaOH (100 mL) with stirring. Aq. layer was extracted with EtOAc and the combined organic layer was washed with 2 N HCl, water, brine, dried and filtered. The solvent was evaporated and the crude product was washed with hexane, to provide the desired aldehyde intermediate as a reddish brown solid (2.1 g, 20%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 6-8 h
  3. temperatureThe dark red solution was cooled to RT
  4. stirringwith stirring
  5. extractionAq. layer was extracted with EtOAc
  6. washthe combined organic layer was washed with 2 N HCl, water, brine
  7. customdried
  8. filtrationfiltered
  9. customThe solvent was evaporated
  10. washthe crude product was washed with hexane

Sources & evidence

ORD record
ord-93062a91aa1e48fc95b71b7e013d7dba
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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