Benzyl Bromide → 3-Benzyloxy-1-propanol

HRID 465628Notes

Reaction equation

HRID 465628 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH2:5][OH:6].[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:8]([O:6][CH2:5][CH2:4][CH2:3][OH:7])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 104421,3-PropanediolHCID 24758Sodium hydride

Product 1

HCID 3479713-Benzyloxy-1-propanol

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (5.6 g, 0.14 mole) in tetrahydrofuran (350 ml) is added 1,3-propanediol (15 ml, 0.21 mol). The gummy suspension is stirred at room temperature for 0.5 hour and tetra n-butylammonium iodide (0.54 g) is added followed by benzyl bromide (16.6 ml, 0.14 mole). The mixture is stirred at room temperature for 62 hours. The solvent is evaporated and the residue purified by flash chromatography over silica gel using 1:4 ethylacetate/hexane as eluent to obtain 3-benzyloxypropan-1-ol as a clear oil; 1H NMR (CDCl3): δ7.3 (m, 5H), 4.5 (s,2H), 3.78 (t,8 Hz,2H), 3.65 (t,8 Hz,2H), 1.87 (quintet,8 Hz,2H).

Workup

  1. stirringThe mixture is stirred at room temperature for 62 hours
  2. customThe solvent is evaporated
  3. customthe residue purified by flash chromatography over silica gel using 1:4 ethylacetate/hexane as eluent

Sources & evidence

ORD record
ord-0eba3a67b25e46d293e0aac2721f530d
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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