L-Lactic Acid → Benzyl lactate

HRID 6411

Reaction equation

HRID 6411 reaction equation
[CH2:1]([C@@](C)(O)C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([OH:19])(=[O:18])[C@H:15]([CH3:17])[OH:16].C(N(CC1C=CC=CC=1)C(=NC(C)C)O)(C)C>C1COCC1>[C:14]([O:19][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:18])[CH:15]([CH3:17])[OH:16]

Participants

5

Reactant 3

HCID 107689L-Lactic AcidHCID 11286816(2R)-2-Hydroxy-2-methyl-3-phenylpropanoic acidHCID 178418581HCID 178418581, compound

Product 1

HCID 98054Benzyl lactateYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

Construction of Benzyl-L-lactic Acid. L-Lactic acid (9 g, 100 mmol) is added to N,N'-diisopropylbenzylisourea (23.3 g, 100 mmol) with stirring. The mixture becomes very viscous within 10 min and is stirred intermittently for 1 h. The volume is then increased to 200 mL with THF, and the mixture stirred for 48 h at room temperature. After cooling the mixture to -15° C., the diisopropylurea is removed by filtration and the THF is evaporated under reduced pressure. The resulting thick oil is pumped under high vacuum for 24 h to give benzyl lactate (17.4 g, 95%) which may be used without further purification.

Workup

  1. stirringis stirred intermittently for 1 h
  2. stirringthe mixture stirred for 48 h at room temperature
  3. customthe diisopropylurea is removed by filtration
  4. customthe THF is evaporated under reduced pressure
  5. waitThe resulting thick oil is pumped under high vacuum for 24 h

Sources & evidence

ORD record
ord-9f8135fc2ea3458ea13011035828fec5
Source dataset
uspto-grants-1993_09
Patent number
US05248761

Linked notes

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