Water → 5-(Benzyloxy)-2-phenyl-1,3-dioxane

HRID 1761737Notes

Reaction equation

HRID 1761737 reaction equation
[H-].[Na+].[C:3]1([CH:9]2[O:14][CH2:13][CH:12]([OH:15])[CH2:11][O:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C)C=O>[CH2:16]([O:15][CH:12]1[CH2:13][O:14][CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[O:10][CH2:11]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 743621,3-Dioxan-5-ol, 2-phenyl-

Product 1

HCID 2630835-(Benzyloxy)-2-phenyl-1,3-dioxaneYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of about 19.63 g of about 50% sodium hydride in about 450 ml of dimethylformamide was added, portionwise, over about 15 minutes about 67 g of 2-phenyl-m-dioxan-5-ol. After stirring about 20 minutes, the mixture was cooled in ice and about 69.95 g of benzyl bromide was added dropwise over about 20 minutes. The mixture was stirred at room temperature overnight, water was added and the solid collected. This solid was dissolved in hot toluene, dried, filtered and diluted with an equal volume of petroleum ether. After standing about 4 hours at about 0° C. the solid was collected, giving about 90.5 g of the desired title compound.

Workup

  1. additionwas added
  2. temperaturethe mixture was cooled in ice
  3. stirringThe mixture was stirred at room temperature overnight
  4. customthe solid collected
  5. dissolutionThis solid was dissolved in hot toluene
  6. customdried
  7. filtrationfiltered
  8. additiondiluted with an equal volume of petroleum ether
  9. waitAfter standing about 4 hours at about 0° C.
  10. customthe solid was collected

Sources & evidence

ORD record
ord-243a60ef9ca645ea9958a6b3c65f49c8
Source dataset
uspto-grants-1989_05
Patent number
US04827011

Reaction notes

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