Lactic Acid → 4-Methoxybenzyl 2-hydroxypropionate

HRID 1790746Notes

Reaction equation

HRID 1790746 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 acatate 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 acatate
  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-456261c7dad64f4b82b109c7e26a8345
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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