Benzyl Bromide → Benzyl 2-hydroxybutanoate

HRID 849740Notes

Reaction equation

HRID 849740 reaction equation
[OH:1][CH:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].[Na].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C=O)C>[OH:1][CH:2]([CH2:6][CH3:7])[C:3]([O:5][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 112662-Hydroxybutyric AcidHCID 5360545Sodium

Product 1

HCID 13908922Benzyl 2-hydroxybutanoateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (±)-2-hydroxybutanoic acid, sodium salt (2.54 g, 20.1 mmol) in dry DMF (30 ml) was added benzyl bromide (2.9 mL, 1.2 eq) and anhydrous KI (330 mg, 0.1 eq). The suspension was heated at 100° C. for 24 hours and the DMF was distilled off under reduced pressure. The residue was taken up in ether, washed with water and saturated Na2S2O3, dried (MgSO4), and concentrated. Distillation of the residual oil afforded 3.7 g (95%) of benzyl (±)-2-hydroxybutanoate as a colorless oil, b.p. 95° C. (0.45 Torr).

Workup

  1. distillationthe DMF was distilled off under reduced pressure
  2. washwashed with water and saturated Na2S2O3
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. distillationDistillation of the residual oil

Sources & evidence

ORD record
ord-9a081e1c71344c398db11c8ebad33cd3
Source dataset
uspto-grants-2000_01
Patent number
US06013792

Reaction notes

Loading…