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Dichloromethane → 2-Methyl-2-{4-[2-(toluene-4-sulfonyloxy)-ethyl]-phenyl}-propionic acid methylester

HRID 451228
Notes
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Reaction equation

HRID 451228 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][OH:15])=[CH:9][CH:8]=1)([CH3:6])[CH3:5].C(N(CC)CC)C.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.ClCCl>O>[CH3:1][O:2][C:3](=[O:16])[C:4]([CH3:6])([C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][O:15][S:30]([C:27]2[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=2)(=[O:32])=[O:31])=[CH:11][CH:12]=1)[CH3:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 45257528Methyl 2-(4-(2-hydroxyethyl)phenyl)-2-methylpropanoate

Product 1

HCID 866497972-Methyl-2-{4-[2-(toluene-4-sulfonyloxy)-ethyl]-phenyl}-propionic acid methylesterYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a reaction vessel, 2-[4-(2-hydroxy-ethyl)-phenyl]-2-methyl-propionic acid methylester (2 g) prepared in the Examples 1-3, triethylamine (1.1 g), p-toluenesulfonylchloride (1.9 g) and dichloromethane (20 mL) were introduced, and the mixture was reacted at room temperature for 1 hour. Distilled water (50 mL) was added thereto, and the mixture was stirred to separate layers. The separated organic layer was dehydrated with Na2SO4, and then condensed by filtration to obtain 2-methyl-2-{4-[2-(toluene-4-sulfonyloxy)-ethyl]-phenyl}-propionic acid methylester (3.0 g, yield 91%).

Workup

  1. additionwere introduced
  2. customthe mixture was reacted at room temperature for 1 hour
  3. customto separate layers
  4. customcondensed
  5. filtrationby filtration

Sources & evidence

ORD record
ord-c6d0c58182314521919f64ee276dd47b
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08487106B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes