Benzyl Bromide → HCID 10487510, compound

HRID 1033430Notes

Reaction equation

HRID 1033430 reaction equation
[H-].[Na+].[CH3:3][C:4]([OH:8])([CH:6]=[CH2:7])[CH3:5].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O1CCCC1>[CH2:9]([O:8][C:4]([CH3:5])([CH:6]=[CH2:7])[CH3:3])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 82572-Methyl-3-buten-2-olHCID 24758Sodium hydride

Product 1

HCID 10487510HCID 10487510, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 18.6 g of 60% sodium hydride oil dispersion (0.46 mol) in 50 mL of dry tetrahydrofuran at 0° C. was added 40 g (0.46 mol) of 2-methyl-3-buten-2-ol over 30 minutes. The resulting mixture was warmed to room temperature and stirred for 3 hours, then heated at reflux for an additional 30 minutes. The mixture was cooled to 0° C., treated with 80 g (0.46 mol) of benzyl bromide, then heated at reflux for 5 hours. The reaction mixture was cooled, filtered and concentrated under vacuum. The residue was purified by distillation under reduced pressure to give 42 g (0.24 mol,52%) of product, b.p. 88°-89° C. (2 mm). 1H NMR (200 MHz,CDCl3): 1.38 (s,6H), 4.39 (s,2H), 5.20 (m,2H), 5.95 (m,1H), 7.2-7.4 (m,5H).

Workup

  1. temperatureheated
  2. temperatureat reflux for an additional 30 minutes
  3. temperatureThe mixture was cooled to 0° C.
  4. temperatureheated
  5. temperatureat reflux for 5 hours
  6. temperatureThe reaction mixture was cooled
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. distillationThe residue was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-14e30591eb8e40e1a418c9ed366428fa
Source dataset
uspto-grants-1994_05
Patent number
US05310737

Reaction notes

Loading…