4-Hydroxybenzaldehyde → HCID 2736334, compound

HRID 2232577Notes

Reaction equation

HRID 2232577 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.[I-].C([NH3+])(C)(C)C.[CH2:18]([CH:20]1[O:22][CH2:21]1)Cl>O1CCCC1>[CH2:18]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)[CH:20]1[O:22][CH2:21]1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 7835EpichlorohydrinHCID 24758Sodium hydride2×HCID 22344722t-Butylammonium Iodide

Product 1

HCID 2736334HCID 2736334, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 250 ml. three neck flask was equipped with magnetic stir bar, reflux condenser, addition funnel and nitrogen inlet. Dry nitrogen was swept through the apparatus while it was heated with a heat gun. After the apparatus was cooled, 5.95 g. of a 60% oil dispersion of sodium hydride (0.149 mole) was added and triturated three times with 25 ml. of petroleum ether to remove the oil. A solution of 36.6 g. (0.3 mole) 4-hydroxybenzaldehyde in 100 ml. of tetrahydrofuran was added dropwise to the sodium hydride over 30 mins. When the addition was complete, 1.1 g. (0.0003 mole) tert-butyl ammonium iodide was added along with 30.7 g. (0.33 mole) epichlorohydrin. The reaction mixture was refluxed overnight, cooled, filtered, and the solvent removed under vacuum. Excess epichlorohydrin was removed by azeotropic distillation using a ten fold excess of toluene. Yield was 40% of 4-glycidoxy benzaldehyde.

Workup

  1. customthree neck flask was equipped with magnetic stir bar
  2. temperaturereflux
  3. additioncondenser, addition funnel and nitrogen inlet
  4. temperaturewas heated with a heat gun
  5. temperatureAfter the apparatus was cooled
  6. customtriturated three times with 25 ml
  7. customof petroleum ether to remove the oil
  8. additionWhen the addition
  9. temperatureThe reaction mixture was refluxed overnight
  10. temperaturecooled
  11. filtrationfiltered
  12. customthe solvent removed under vacuum
  13. customExcess epichlorohydrin was removed by azeotropic distillation

Sources & evidence

ORD record
ord-afd2cade880d41b29912abc869301652
Source dataset
uspto-grants-1988_11
Patent number
US04788280

Reaction notes

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