Benzyl Bromide → ((3-Chloropropoxy)methyl)benzene

HRID 1252565Notes

Reaction equation

HRID 1252565 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][OH:5].[CH2:6](Br)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CC(C)([O-])C.[K+]>C1COCC1>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 123133-Chloro-1-propanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 221505((3-Chloropropoxy)methyl)benzeneYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a 2 l flask, a mixture of 3-chloropropanol (56.7 g), benzyl bromide (102.6 g) and dry THF (600 ml) is stirred and cooled with ice/salt mixture. Potassium tert-butoxide (70 g) is added in portions (5-10 g), maintaining the internal temperature at about 0° C. After the mixture is stirred for 3 more hours at room temperature, the solvent is evaporated. Addition of 1N HCl (1 l), extraction with ether (1 l), and evaporation of solvent gives crude material (113.6 g), which is distilled under vacuum to give 1-chloro-3-benzyloxypropane (108.4 g) b.p.0.01 60°-80° C.

Workup

  1. temperaturecooled with ice/salt mixture
  2. stirringAfter the mixture is stirred for 3 more hours at room temperature
  3. customthe solvent is evaporated
  4. additionAddition of 1N HCl (1 l), extraction
  5. customwith ether (1 l), and evaporation of solvent
  6. customgives crude material (113.6 g), which
  7. distillationis distilled under vacuum

Sources & evidence

ORD record
ord-b483449bc0fd4f7599dd80dfb18cf900
Source dataset
uspto-grants-1988_05
Patent number
US04743691

Reaction notes

Loading…