Benzyl Chloride → Methyl 2-(benzyloxy)propanoate

HRID 512810

Reaction equation

HRID 512810 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[CH:2]([CH3:4])[OH:3].[CH2:8](Cl)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC(C)([O-])C.[Na+]>CN(C)C=O>[CH2:8]([O:3][CH:2]([CH3:4])[C:1]([O:6][CH3:7])=[O:5])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11040Methyl LactateHCID 23676156Sodium t-butoxide

Product 1

HCID 561764Methyl 2-(benzyloxy)propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
30 °C

Procedure

To a pre-cooled solution of racemic methyl lactate (200 g) in dimethyl formamide (400 ml) at 0-10° C., added benzyl chloride (218.8 g). Sodium tertiary butoxide (224.6 g) was added to the reaction mixture at 0-10° C. and stirred for 6 hours at 25-35° C. After completion of the reaction, the reaction mixture was quenched with water and extracted with toluene. The toluene layer was washed with water followed by 10% sodium chloride solution. The obtained toluene layer containing title compound was taken to next step.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mixture was quenched with water
  3. extractionextracted with toluene
  4. washThe toluene layer was washed with water
  5. additionThe obtained toluene layer containing title compound

Sources & evidence

ORD record
ord-a26405a450844edfbca5095bd1d67402
Source dataset
uspto-grants-2015_08
Patent number
US09102664B2

Linked notes

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