Lactic Acid → 4-Methoxybenzyl 2-hydroxypropionate

HRID 1170580Notes

Reaction equation

HRID 1170580 reaction equation
[OH:1][CH:2]([CH3:6])[C:3]([OH:5])=[O:4].CC(C)([O-])C.[K+].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1>CN(C=O)C>[OH:1][CH:2]([CH3:6])[C:3]([O:5][CH2:19][C:18]1[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1)=[O:4]

Participants

5

Reactant 3

HCID 612Lactic AcidHCID 699934-Methyloxybenzyl chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 220357644-Methoxybenzyl 2-hydroxypropionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of DL-2 hydroxypropionic acid (9.0 g, 100 mmole) in 100 ml dry DMF was added potassium tert-butoxide (12.34 g, 110 mmole) and the mixture was stirred for one hour at 60° C. 4-methoxybenzyl chloride (18.8 g 120 mmole) was added and the mixture was stirred for eight hours at 60° C. The mixture was evaporated under reduced pressure and 250 ml ethyl acetate was added. The organic phase was washed four times with water. The organic phase was dried with sodium sulfate and concentrated in vacuo. Yield: 16.8 g

Workup

  1. stirringthe mixture was stirred for eight hours at 60° C
  2. customThe mixture was evaporated under reduced pressure and 250 ml ethyl acetate
  3. additionwas added
  4. washThe organic phase was washed four times with water
  5. dry with materialThe organic phase was dried with sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7be62212e7414d828be9ee7e08fad06e
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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