Benzene → HCID 20786401, compound

HRID 2182862Notes

Reaction equation

HRID 2182862 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([S:23]([CH2:26][CH2:27]O)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C[C:30]1[CH:31]=[CH:32][C:33]([S:36]([OH:39])(=[O:38])=O)=[CH:34][CH:35]=1.O.[CH:41]1C=CC=C[CH:42]=1>>[C:17]1([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][CH2:41][CH2:42][S:36]([C:33]2[CH:34]=[CH:35][CH:30]=[CH:31][CH:32]=2)(=[O:38])=[O:39])=[O:15])(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 302022-(Phenylsulfonyl)ethanolHCID 794272,2'-(1,2-Phenylenebis(oxy))bisacetic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 20786401HCID 20786401, compoundYield 99%

Procedure

A mixture of 1,2-phenylenedioxydiacetic acid (available from Aldrich, 3.0 g, 13.3 mmol), 2-(phenylsulfonyl)ethanol (5.0 g, 26.5 mmol), and p-TsOH.H2O (0.5 g) in 100 mL of benzene was heated overnight to reflux temperature with a Dean-Stark trap. Thereafter the mixture was concentrated by evaporation under reduced pressure, water was added and the mixture was extracted with CH2Cl2. The combined organic layers were washed with saturated NaHCO3 solution and water, dried, and concentrated under reduced pressure. The resulting residual oil was purified by short path column chromatography (silica gel, CH2Cl2) to give Intermediate 28 (7.4 g, 99%) as a light brown oil.

Workup

  1. temperaturewas heated overnight
  2. temperatureto reflux temperature with a Dean-Stark trap
  3. concentrationThereafter the mixture was concentrated by evaporation under reduced pressure, water
  4. additionwas added
  5. extractionthe mixture was extracted with CH2Cl2
  6. washThe combined organic layers were washed with saturated NaHCO3 solution and water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residual oil was purified by short path column chromatography (silica gel, CH2Cl2)

Sources & evidence

ORD record
ord-316f098935814e6d98f6b1803e0126d6
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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