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4-Methyloxybenzyl chloride → HCID 11095877, compound

HRID 989924
Notes
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Reaction equation

HRID 989924 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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. 4Methoxybenzyl 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 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: 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 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-19c413e113a94f7bb5c0181f0e129f86
Source dataset
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06458772B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes