4-Toluenesulfonyl chloride → 3-Propionylphenyl 4-methylbenzenesulfonate

HRID 1040296Notes

Reaction equation

HRID 1040296 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:11])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>ClCCl>[C:8]([C:4]1[CH:3]=[C:2]([O:1][S:24]([C:21]2[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=2)(=[O:26])=[O:25])[CH:7]=[CH:6][CH:5]=1)(=[O:11])[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 831413'-Hydroxypropiophenone

Product 1

HCID 866910613-Propionylphenyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
32.5 °C

Procedure

To a stirred suspension of 1-(3-hydroxy-phenyl)-propan-1-one (2 kg, 13.32 mol) and potassium carbonate (3.681 kg, 26.64 mol) in dichloromethane (20 L), p-toluenesulfonyl chloride (2.8 kg, 14.65 mol) was added at 30-35° C. The reaction mixture was stirred at 30-35° C. for 1 hour. Reaction mixture was diluted with dichloromethane (10 L) and washed with water (2×10 L). Dichloromethane layer separated, dried and solvent distilled off to give title compound. Cyclohexane (10 L) was added to the resulting product at 65-70° C. and stirred for 2 hours. Mixture was cooled to ambient temperature, filtered and dried to give 3.87 kg the title compound.

Workup

  1. additionwas added at 30-35° C
  2. customReaction mixture
  3. washwashed with water (2×10 L)
  4. customDichloromethane layer separated
  5. customdried
  6. distillationsolvent distilled off

Sources & evidence

ORD record
ord-e28dff9e973a4020bec5ff767f624a29
Source dataset
uspto-grants-2013_10
Patent number
US08552219B2

Reaction notes

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