Benzyl Alcohol → Benzyl 3-bromopropanoate

HRID 343463Notes

Reaction equation

HRID 343463 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.[Br:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17].C(O)C1C=CC=CC=1>C1C=CC=CC=1>[CH2:12]([O:18][C:16](=[O:17])[CH2:15][CH2:14][Br:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 115533-Bromopropionic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 252570Benzyl 3-bromopropanoateYield 56%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A spatula tip full of p-toluenesulfonic acid monohydrate was added to a solution of 3-bromopropionic acid (20.49 g, 0.134 mol) and benzyl alcohol (15 mL, ~15.7 g, 0.145 mol) in benzene (150 mL). A Dean-Stark trap was fitted to the reaction vessel and the solution was held at reflux with overnight stirring. After 16 hr at reflux, the reaction was cooled, washed with saturated sodium bicarbonate, dried (Na2SO4), and concentrated to an oil (28.78 g). Fractional distillation at reduced pressure (0.18 torr) gave the desired product as a colorless liquid (18.49 g, 56%) boiling in the range 99°-109° C.

Workup

  1. customA Dean-Stark trap was fitted to the reaction vessel
  2. temperatureat reflux with overnight
  3. temperatureAfter 16 hr at reflux
  4. temperaturethe reaction was cooled
  5. washwashed with saturated sodium bicarbonate
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to an oil (28.78 g)
  8. distillationFractional distillation at reduced pressure (0.18 torr)

Sources & evidence

ORD record
ord-c7e51193a5394d8895bd4e787eef79d9
Source dataset
uspto-grants-1999_01
Patent number
US05861428

Reaction notes

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