Sodium Azide → [4-(Azidomethyl)phenyl]methanol
Reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=1.[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C>[N:11]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=1)=[N+:12]=[N-:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of (4-Chloromethyl-phenyl)-methanol (5 g, 31.9 mmol) and sodium azide (2.283 g, 35.1 mmol) in 50 mL DMF was stirred at 90° C. for 16 h. The reaction mixture was concentrated in vacuo and the residue was treated with DCM and extracted with water. The organic layer was dried over MgSO4 and evaporated to give the title compound which was used in the next step without further purification. 1H-NMR (CDCl3, 400 MHz) 7.38-7.31 (m, 4H), 4.52 (d, 2H, 5.6 Hz), 4.42 (s, 2H).
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- additionthe residue was treated with DCM
- extractionextracted with water
- dry with materialThe organic layer was dried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-dd8389899fe244398f1a6b4ddea79d24
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09290485B2
Reaction notes
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