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

HRID 1607754Notes

Reaction equation

HRID 1607754 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-10b47b92bf4148578689f32ad145f79c
Source dataset
uspto-grants-1989_09
Patent number
US04866206

Reaction notes

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