Water → 4-(3-Azidopropyloxy)benzaldehyde

HRID 1107718Notes

Reaction equation

HRID 1107718 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.[N-:14]=[N+:15]=[N-:16].[Na+].O>CS(C)=O>[N:14]([CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1)=[N+:15]=[N-:16]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 137157894-(3-Bromopropoxy)benzaldehyde

Product 1

HCID 187858194-(3-Azidopropyloxy)benzaldehydeYield 92.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-(3-bromopropyloxy)benzaldehyde (3.5 g, 14.5 mmol) and sodium azide (29 mmol, 1.9 g) in DMSO (70 ml) was stirred for 16 h, poured into water (100 ml) and extracted twice with diethyl ether. The extracts were washed with water (50 ml) and saturated aqueous sodium chloride, dried over sodium sulphate and evaporated to give a colourless oil (2.75 g). M+ 205; 360 MHz 1H n.m.r (CDCl3) 7.84 (2H, d, J 11 Hz), 7.02 (2H, d, J 11 Hz), 4.14 (2H, t, J 5.9 Hz), 3.55 (2 H, t, J 6.5 Hz), 2.09 (2 H, app. pentet, J 6.2 Hz).

Workup

  1. extractionextracted twice with diethyl ether
  2. washThe extracts were washed with water (50 ml) and saturated aqueous sodium chloride
  3. dry with materialdried over sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-a05c1f43996841eb8a8fe4f72947522a
Source dataset
uspto-grants-2000_05
Patent number
US06063789

Reaction notes

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