4-Methyloxybenzyl chloride → HCID 11095877, compound

HRID 1170577Notes

Reaction equation

HRID 1170577 reaction equation
[OH:1][C@@H: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][C@@H: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 699934-Methyloxybenzyl chlorideHCID 107689L-Lactic AcidHCID 23665647Potassium tert-butoxide

Product 1

HCID 11095877HCID 11095877, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of (S)(+)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 25° C. 4-Methoxybenzyl chloride (18.8 g 120 mmole) was added and the mixture was stirred for six 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: 15.6 g=74%

Workup

  1. stirringthe mixture was stirred for six 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-26e9f895c5734757b19474036fa81fb8
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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