4-Toluenesulfonyl chloride → 3-(4-Methylphenyl)propyl 4-methylbenzene-1-sulfonate

HRID 2240587Notes

Reaction equation

HRID 2240587 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].C(NC(C)C)(C)C.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][OH:28])=[CH:21][CH:20]=1.[Cl-].[NH4+]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:19]1([CH3:29])[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][CH2:27][O:28][S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 2218933-(4-Methylphenyl)propan-1-ol

Product 1

HCID 539033013-(4-Methylphenyl)propyl 4-methylbenzene-1-sulfonateYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2.46 g of tosyl chloride (13 mM), 3.4 ml of diisopropylamine (19.4 mM) and 158 mg of 4-(dimethylamino)pyridine (1.29 mM) were added to reaction solution (6.46 mM) dissolving 971 mg of 3-p-tolyl-propane-1-ol (40ac) prepared by above step 3 in methylene chloride at 0° C. under Ar atmosphere with stirring for 6 hrs, and the reaction mixture was stirred for 12 hrs at room temperature. After the reaction mixture was neutralized with ammonium chloride, the mixture was extracted with ethyl acetate, washed with saturated NaCl solution, dried over MgSO4, filtered, and concentrated in vacuo. The resultant was purified by Silica gel column chromatography with a solvent mixture mixed with methanol and chloroform (1:7) as an eluant to give 1.3 g of toluene-4-sulfonate-3-p-tolyl-propyl ester (40ad) (yield: 70%).

Workup

  1. stirringthe reaction mixture was stirred for 12 hrs at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resultant was purified by Silica gel column chromatography with a solvent mixture
  8. additionmixed with methanol and chloroform (1:7) as an eluant

Sources & evidence

ORD record
ord-4c866b7f470947938e6e6aeda29eeaa8
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Reaction notes

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