3-Hydroxybenzaldehyde → HCID 20482781, compound

HRID 2095262Notes

Reaction equation

HRID 2095262 reaction equation
I[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[OH:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17]>O1CCOCC1>[C:2]1([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[CH:16]=[O:17])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1013-HydroxybenzaldehydeHCID 70041-Iodonaphthalene

Product 1

HCID 20482781HCID 20482781, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

1-iodonaphthalene (2.000 g) and 3-hydroxybenzaldehyde (1.442 g) were added to dioxane (25 mL). The solution was degassed and flushed with nitrogen three times. Cesium carbonate (5.13 g), N, N-dimethylglycine hydrochloride (82 mg), and copper (I) iodide (30 mg) were added, and the solution was heated at 90° C. overnight. The solution was cooled, added to 1M aqueous HCl, extracted with diethyl ether, dried with brine and anhydrous sodium sulfate. The solution was concentrated and purified by flash column chromatography on silica gel with 10% ethyl acetate in hexanes to provide the title compound.

Workup

  1. customThe solution was degassed
  2. customflushed with nitrogen three times
  3. additionCesium carbonate (5.13 g), N, N-dimethylglycine hydrochloride (82 mg), and copper (I) iodide (30 mg) were added
  4. temperatureThe solution was cooled
  5. additionadded to 1M aqueous HCl
  6. extractionextracted with diethyl ether
  7. dry with materialdried with brine and anhydrous sodium sulfate
  8. concentrationThe solution was concentrated
  9. custompurified by flash column chromatography on silica gel with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6f460a3b3dd6492a847a8077026ad9b4
Source dataset
uspto-grants-2013_05
Patent number
US08445679B2

Reaction notes

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