4-Toluenesulfonyl chloride → HCID 87111133, compound

HRID 1468245Notes

Reaction equation

HRID 1468245 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[O:14][CH3:15].C(=O)([O-])[O-].[Na+].[Na+].[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>C1CCCCC1>[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([O:1][CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=2[O:14][CH3:15])(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 43393692HCID 43393692, compound

Product 1

HCID 87111133HCID 87111133, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
27.5 °C

Procedure

To 50 gms (0.24 mole) of 4-(3′-Hydroxypropoxy)-3-methoxy benzonitrile in 200 ml. of cyclohexane was added 26 gms (0.24 mole) of sodium carbonate and 46 gms (0.24 mole) of p-toluene sulfonyl chloride at once. The resultant reaction mixture was refluxed for about 4-6 hrs. After completion of the reaction, the reaction mass was cooled to about 25-30° C. and the inorganic salts were filtered off. and washed with cyclohexane. The solvents were distilled completely and solid obtained was recrystallized from 150 ml of ethyl acetate to afford the title compound as white crystalline powder.

Workup

  1. customThe resultant reaction mixture
  2. temperaturewas refluxed for about 4-6 hrs
  3. customAfter completion of the reaction
  4. filtrationthe inorganic salts were filtered off
  5. washand washed with cyclohexane
  6. distillationThe solvents were distilled completely
  7. customsolid obtained
  8. customwas recrystallized from 150 ml of ethyl acetate

Sources & evidence

ORD record
ord-1e8d6dbd69be467ead984d6eda34a514
Source dataset
uspto-grants-2015_04
Patent number
US09000221B2

Reaction notes

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