Water → HCID 68906541, compound

HRID 217297Notes

Reaction equation

HRID 217297 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:12][C:13]1[CH:20]=[C:19]([CH2:21]O)[C:18]([CH2:23][CH2:24][OH:25])=[CH:17][C:14]=1[C:15]#[N:16].ClC1C(CCO)=C(CO)C=CC=1C#N.O>C1(C)C=CC=CC=1>[Cl:12][C:13]1[CH:20]=[C:19]2[C:18]([CH2:23][CH2:24][O:25][CH2:21]2)=[CH:17][C:14]=1[C:15]#[N:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 68906302HCID 68906302, compoundHCID 68908782HCID 68908782, compound

Product 1

HCID 68906541HCID 68906541, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

p-Toluene sulfonic acid (0.76 g, 5.4 mmol) was added to a solution of a mixture (0.57 g, 2.7 mmol) of 2-chloro-5-(2-hydroxyethyl)-4-hydroxymethylbenzonitrile and 2-chloro-3-(2-hydroxyethyl)-4-hydroxymethylbenzonitrile in toluene (10 mL). The mixture was stirred while heating under reflux overnight. The reaction solution was cooled to room temperature, and water was added thereto. The mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give crude product. The resulting crude product was purified by silica gel column chromatography using n-hexane-ethyl acetate (mixing ratio=2:1), and dried under reduced pressure to give a 1:0.1 mixture (0.4 g, 79%) of the title compound and 5-chloroisochromane-6-carbonitrile.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux overnight
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give crude product
  7. customThe resulting crude product was purified by silica gel column chromatography
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-69b257bcab2545ad87933199ba19ac28
Source dataset
uspto-grants-2012_06
Patent number
US08193351B2

Reaction notes

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