Hydrochloric Acid → 2,2-Dimethyl-3-oxobutyl 4-methylbenzene-1-sulfonate

HRID 464918Notes

Reaction equation

HRID 464918 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][C:13]([CH3:19])([C:16](=[O:18])[CH3:17])[CH2:14][OH:15].N1C=CC=CC=1.Cl>C(Cl)(Cl)Cl>[CH3:12][C:13]([CH3:19])([C:16](=[O:18])[CH3:17])[CH2:14][O:15][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 111943184-Hydroxy-3,3-dimethylbutan-2-one

Product 1

HCID 125900172,2-Dimethyl-3-oxobutyl 4-methylbenzene-1-sulfonateYield 71%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

47.6 g (0.25 mol) of 4-toluenesulphonyl chloride were dissolved in 100 ml of chloroform, 35 g (0.3 mol) of 2,2-dimethyl-1-hydroxy-butan-3-one were added, and 40 ml (0.5 mol) of pyridine were added dropwise at 0° to 50° C. The reaction mixture was subsequently stirred at room temperature for 15 hours and poured on to 200 g of ice and 70 ml of concentrated hydrochloric acid and the organic phase was separated off, rinsed three times with 200 ml of water each time, dried over sodium sulphate and concentrated. The residue was taken up in 100 ml of petroleum ether, whereupon the end product crystallized out. 46 g (71% of theory) of 2,2-dimethyl-1-tosyloxy-butan-3-one were obtained as colorless crystals of melting point 49° to 52° C. ##STR815##

Workup

  1. customthe organic phase was separated off
  2. washrinsed three times with 200 ml of water each time
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customcrystallized out

Sources & evidence

ORD record
ord-ed9a075655514ee0b40ce28ab902d324
Source dataset
uspto-grants-1985_10
Patent number
US04549900

Reaction notes

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