Water → 3-(2-Methoxyphenyl)propionic acid 2-(toluene-4-sulfonyl)ethyl ester

HRID 2182880Notes

Reaction equation

HRID 2182880 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][C:11]([OH:13])=[O:12].[C:14]1([CH3:26])[CH:19]=[CH:18][C:17]([S:20]([CH2:23][CH2:24]O)(=[O:22])=[O:21])=[CH:16][CH:15]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[C:14]1([CH3:26])[CH:19]=[CH:18][C:17]([S:20]([CH2:23][CH2:24][O:12][C:11](=[O:13])[CH2:10][CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 806523-(o-Methoxyphenyl)propionic acidHCID 89682Ethanol, 2-[(4-methylphenyl)sulfonyl]-HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 207864443-(2-Methoxyphenyl)propionic acid 2-(toluene-4-sulfonyl)ethyl esterYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(2-methoxyphenyl)propionic acid (5.0 g, 27.8 mmol), 2-(p-toluenesulfonyl)ethanol (5.5 g, 27.8 mmol), and p-toluenesulfonic acid hydrate (p-TsOH.H2O) (0.5 g) in 100 mL of toluene was refluxed with Dean-Stark trap for 5 h. Then water was added and the mixture was extracted with CH2Cl2. The combined organic layers were washed with saturated NaHCO3 solution (2×), dried over MgSO4, and concentrated to give 3-(2-methoxyphenyl)propionic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 59, 5.5 g, 88%) as a light brown liquid.

Workup

  1. temperaturewas refluxed with Dean-Stark trap for 5 h
  2. extractionthe mixture was extracted with CH2Cl2
  3. washThe combined organic layers were washed with saturated NaHCO3 solution (2×)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-116cb1b7e76345cf9d20877c1b849082
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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