Benzyl Alcohol → benzyl (2S)-2-hydroxypropanoate

HRID 1858907Notes

Reaction equation

HRID 1858907 reaction equation
C[C@@H:2]1[O:9][C:7](=[O:8])[C@H:6]([CH3:10])[O:5][C:3]1=O.O.[C:12]1(C)[CH:17]=[CH:16]C(S(O)(=O)=O)=[CH:14][CH:13]=1.C(O)C1C=CC=CC=1>>[C:7]([O:9][CH2:2][C:3]1[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=1)(=[O:8])[C@H:6]([CH3:10])[OH:5]

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 107983Lactide, L-HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 11052238benzyl (2S)-2-hydroxypropanoate

Procedure

Commercially available L-lactide 1 (16 g, 0.14 mol) and p-toluenesulfonic acid monohydrate (catalytic amount) in benzyl alcohol (40 mL, 0.38 mol) was heated to 110° C. overnight. Excess benzyl alcohol was removed under vacuum to obtain a light yellow oil. The desired product was distilled under vacuum (0.9 mm Hg, 85-95° C.) to obtain 50.3 g of 2 as a clear oil. The distilled oil was used without further purification.

Workup

  1. customExcess benzyl alcohol was removed under vacuum
  2. customto obtain a light yellow oil
  3. distillationThe desired product was distilled under vacuum (0.9 mm Hg, 85-95° C.)

Sources & evidence

ORD record
ord-efedc071ea394426850567736d9af533
Source dataset
uspto-grants-2000_11
Patent number
US06153596

Reaction notes

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