Water → 4-(Hexyloxy)naphthalene-1-carbaldehyde

HRID 2092957Notes

Reaction equation

HRID 2092957 reaction equation
O=P(Cl)(Cl)Cl.[CH2:6]([O:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[C:23](O[Na])(C)=[O:24].O>CN(C=O)C>[CH2:6]([O:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH:23]=[O:24])=[CH:15][CH:14]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 30172091-(Hexyloxy)naphthaleneHCID 178418247HCID 178418247, compound

Product 1

HCID 30169154-(Hexyloxy)naphthalene-1-carbaldehydeYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

POCl3 (3.22 g, 21 mmol) was dropwise added to a solution of compound 2 (4 g, 17.5 mmol) in anh. DMF (5 ml) at room temperature and under N2. The resulting dark red solution was heated to 100° C. for 3 hours. Concentrated AcONa solution (5 ml) was then added and heating was continued for 2 hours more. After being cooled to room temperature, water (100 ml) was added. The mixture was extracted with Et2O (2×150 ml), the ethereal combined fractions were washed with 10% HCl solution (100 ml), water (100 ml), dried over MgSO4, filtered and evaporated to dryness. Recrystallisation of the brown solid from EtOH afford 2.1 g (47%) of compound 3 as brownish crystals.

Workup

  1. temperatureheating
  2. temperatureAfter being cooled to room temperature
  3. extractionThe mixture was extracted with Et2O (2×150 ml)
  4. washwere washed with 10% HCl solution (100 ml), water (100 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customRecrystallisation of the brown solid from EtOH

Sources & evidence

ORD record
ord-b052e601d3e74469b1292572f120e6f1
Source dataset
uspto-grants-2013_05
Patent number
US08440843B2

Reaction notes

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