Toluene → {2-[2-(Toluene-4-sulfonyl)-ethoxycarbonylmethoxy]-phenoxy}-acetic acid 2-(toluene-4-sulfonyl)ethyl ester

HRID 2182869Notes

Reaction equation

HRID 2182869 reaction equation
[C:1]1([O:12][CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]([OH:11])=[O:10].[C:17]1([CH3:29])[CH:22]=[CH:21][C:20]([S:23]([CH2:26][CH2:27]O)(=[O:25])=[O:24])=[CH:19][CH:18]=1.[C:30]1([CH3:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O.C1(C)C=C[C:41]([S:44](O)(=[O:46])=[O:45])=[CH:40]C=1>O>[C:17]1([CH3:29])[CH:22]=[CH:21][C:20]([S:23]([CH2:26][CH2:27][O:10][C:9](=[O:11])[CH2:8][O:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[O:12][CH2:13][C:14]([O:16][CH2:40][CH2:41][S:44]([C:33]2[CH:34]=[CH:35][C:30]([CH3:36])=[CH:31][CH:32]=2)(=[O:46])=[O:45])=[O:15])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 794272,2'-(1,2-Phenylenebis(oxy))bisacetic acidHCID 89682Ethanol, 2-[(4-methylphenyl)sulfonyl]-HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 20786414{2-[2-(Toluene-4-sulfonyl)-ethoxycarbonylmethoxy]-phenoxy}-acetic acid 2-(toluene-4-sulfonyl)ethyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,2-Phenylenedioxydiacetic acid (available from Aldrich, 5 g, 22.1 mmole) and 2-(p-tolylsulfonyl)ethanol (available from Aldrich, 8.8 g, 44.2 mmole) were added to toluene (100 mL). Catalytic amounts of p-toluenesulfonic acid hydrate (0.5 g) were added and the reaction mixture was refluxed with removal of water, using Dean-Stark trap. After 6 hr of reflux, the toluene was distilled off. The residual material was dissolved in dichloromethane (250 mL) and washed with water (200 mL), and 6 N sodium bicarbonate solution (150 mL). The dichloromethane layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to yield 13 g (99%) of {2-[2-(toluene-4-sulfonyl)-ethoxycarbonylmethoxy]-phenoxy}-acetic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 37)

Workup

  1. temperatureAfter 6 hr of reflux
  2. distillationthe toluene was distilled off
  3. dissolutionThe residual material was dissolved in dichloromethane (250 mL)
  4. washwashed with water (200 mL), and 6 N sodium bicarbonate solution (150 mL)
  5. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8945fb62816e40ce8f84d0d0a7383aa3
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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