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

HRID 1995916Notes

Reaction equation

HRID 1995916 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 5° C. The reaction mixture was subsequently stirred at room temperature for 15 hours and poured onto 200 g of ice and 70 ml of concentrated hydrochloric acid and the organic phase was separated off, washed 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. 48 g (71% of theory) of 2,2-dimethyl-1-tosyloxy-butan-3-one were obtained as colorless crystals of melting point 49°-52° C.

Workup

  1. customthe organic phase was separated off
  2. washwashed 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-263f5ac8e461416193ac600abbe1daef
Source dataset
uspto-grants-1983_09
Patent number
US04406909

Reaction notes

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