Water → 3-Isopropyl-5-methylphenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester

HRID 2182885Notes

Reaction equation

HRID 2182885 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:12]=[C:13]([CH3:15])[CH:14]=1)[O:7][CH2:8][C:9]([OH:11])=[O:10])([CH3:3])[CH3:2].[C:16]1([CH3:28])[CH:21]=[CH:20][C:19]([S:22]([CH2:25][CH2:26]O)(=[O:24])=[O:23])=[CH:18][CH:17]=1.O>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:16]1([CH3:28])[CH:21]=[CH:20][C:19]([S:22]([CH2:25][CH2:26][O:10][C:9](=[O:11])[CH2:8][O:7][C:6]2[CH:12]=[C:13]([CH3:15])[CH:14]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=2)(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 89682Ethanol, 2-[(4-methylphenyl)sulfonyl]-HCID 167698883-Isopropyl-5-methylphenoxyacetic acid

Product 1

HCID 695577283-Isopropyl-5-methylphenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3-isopropyl-5-methylphenoxyacetic acid (prepared above, 6.0 g, 28.8 mmol), 2-(p-toluenesulfonyl)ethanol (5.77 g, 28.8 mmol), and p-toluenesulfonic acid hydrate (p-TsOH.H2O) (0.5 g) in 100 mL of toluene was refluxed with Dean-Stark trap for 3 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-isopropyl-5-methylphenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 64, 11.0 g, 98%) as a light brown oil.

Workup

  1. temperaturewas refluxed with Dean-Stark trap for 3 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-354ac88910fe4c028c65a2ff829b7856
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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