Dimethylformamide → 3-Benzyloxy-1-propanol

HRID 1249902Notes

Reaction equation

HRID 1249902 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].CN(C=O)C.[H-].[Na+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O.C1COCC1>[CH2:13]([O:4][CH2:3][CH2:2][CH2:1][OH:5])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 104421,3-PropanediolHCID 24758Sodium hydride

Product 1

HCID 3479713-Benzyloxy-1-propanolYield 51.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 50.0 g (0.657 mol) of 1,3-propandiol 11 in 500 mL of cosolvent (DMF : THF=3:1) in an ice bath was carefully added 26.3 g (0.657 mol) of 60% sodium hydride and stirred for 1 hour, followed by slow addition of 80.5 g (0.636 mol) of benzyl chloride at 0° C. and stirring at room temperature overnight. After adding 50 mL of water to quench the reaction, the mixture was extracted with ether (2×600 mL). The organic layer was washed with water (50 mL) and Brine (50 mL), dried over anhydrous sodium sulfate and concentrated. Distillation at 118-120° C./5 mmHg gave 54.8 g of a liquid in 50.2% yield. 1H NMR (CDCl3): δ 7.35-7.28 (m, 5H, ArH), 4.51 (s, 2H, ArCH2O), 3.76 (m, 2H, CH2O), 3.65 (t, J=6.0 Hz, 2H, CH2O), 2.58 (m, 1H, OH), 1.85 (p, J=6.0 Hz, 2H, CH2). 13C NMR (CDCl3): δ 137.93, 128.34, 127.60, 127.54, 73.15, 69.15, 61.58, 32.04.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ether (2×600 mL)
  4. washThe organic layer was washed with water (50 mL) and Brine (50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. distillationDistillation at 118-120° C./5 mmHg

Sources & evidence

ORD record
ord-68b18876e3084ba4b8648fe21fc168d1
Source dataset
uspto-grants-2002_01
Patent number
US06335364B1

Reaction notes

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