Lactic Acid → 4-Methoxybenzyl 2-hydroxypropionate

HRID 989926Notes

Reaction equation

HRID 989926 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>>[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

4

Reactant 3

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

Product 1

HCID 220357644-Methoxybenzyl 2-hydroxypropionate

Conditions

Temperature
60 °C

Procedure

To a stirred solution of DL-2 hydroxypropionic acid (9.0 g, 100 mmole) in 100 ml dry DMP was added potassium tert-butoxide (12.34 g, 110 mmole) and the mixture was stirred for one hour at 60° C. 4-methoxybenzyl chloride was (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. additionwas added
  2. stirringthe mixture was stirred for eight hours at 60° C
  3. customThe mixture was evaporated under reduced pressure and 250 ml ethyl acatate
  4. additionwas added The organic phase
  5. washwas washed four times with water
  6. dry with materialThe organic phase was dried with sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fac7eeeb1fa54b4d8cdc936a72ade1f3
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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