Sodium Azide → [4-(Azidomethyl)phenyl]methanol

HRID 2097351Notes

Reaction equation

HRID 2097351 reaction equation
Cl[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C>[N:11]([CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1)=[N+:12]=[N-:13]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 5107660[4-(Chloromethyl)phenyl]methanol

Product 1

HCID 23132430[4-(Azidomethyl)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(Chloromethyl)-benzylalcohol (5.01 g, 32 mmol) and NaN3 (2.50 g, 38.4 mmol) were stirred in DMF (25 mL) at 90° C. for 17 h. The solvent was removed under reduced pressure and the residue was partitioned between water (50 mL) and Et2O (100 mL). The aqueous layer was extracted with Et2O (2×50 mL) and the combined org. layers were dried over Na2SO4. After filtration the solvent was removed under reduced pressure to give (4-azidomethyl-phenyl)-methanol, pure enough for further reaction.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between water (50 mL) and Et2O (100 mL)
  3. extractionThe aqueous layer was extracted with Et2O (2×50 mL)
  4. dry with materiallayers were dried over Na2SO4
  5. filtrationAfter filtration the solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-635be607b40b4870834f8bde960324e4
Source dataset
uspto-grants-2013_05
Patent number
US08450348B2

Reaction notes

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