Benzyl Bromide → Benzyl glycidyl ether

HRID 2393931Notes

Reaction equation

HRID 2393931 reaction equation
[H-].[Na+].[CH2:3]1[O:5][CH:4]1[CH2:6][OH:7].[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C=O)C.[I-].C([NH3+])CCC>[CH2:8]([O:7][CH2:6][CH:4]1[O:5][CH2:3]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11164GlycidolHCID 24758Sodium hydride

Product 1

HCID 94247Benzyl glycidyl etherYield 71%

Reagents, catalysts & solvents 2

HCID 21894792HCID 21894792, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Sodium hydride (60% oil dispersion, 23.6 g, 0.59 mol) was added in portions to a solution of glycidol (14) (40 g, 0.54 mol), benzyl bromide (101.5 g, 0.59 mol), and n-butylammonium iodide (0.24 g) in dry DMF (150 mL) at 25° C. (Step 12). The mixture was stirred for 1 hr at 65° C., poured over ice and then extracted with ether (2×75 mL). The combined ether extract was washed with water (3×75 mL) and dried over MgSO4. Distillation using a 12-in vigreux column afforded 62.9 g (71%) of glycidyl ##STR7## benzyl ether 15; bp 120°-122° C. (10 mm); 1H NMR (CDCl3) δ 2.6 (dd, 1H, OCHa), 2.8 (dd, 1H, OCHb), 3.2 (m, 1H, OCHc), 3.2 (dd, 1H, OCHd), 3.8 (dd, 1H, OCHe), 4.6 (dd, 2H, OCH2), 7.23 (s, 5H, phenyl).

Workup

  1. additionpoured over ice
  2. extractionextracted with ether (2×75 mL)
  3. extractionThe combined ether extract
  4. washwas washed with water (3×75 mL)
  5. dry with materialdried over MgSO4
  6. distillationDistillation

Sources & evidence

ORD record
ord-d8189693054d4c909161b9e21dbee86b
Source dataset
uspto-grants-1998_09
Patent number
US05808146

Reaction notes

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