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

HRID 2418206Notes

Reaction equation

HRID 2418206 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 introduced dropwise at 0° to 5° C. The reaction mixture was then stirred for 15 hours at room temperature and was poured onto 200 g of ice and 70 ml of concentrated hydrochloric acid, and the organic phase was separated off, washed with three times 200 ml of water, 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°-52° C. ##STR11##

Workup

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

Sources & evidence

ORD record
ord-bb9723b1f3c94c65ba325a9d2bb26fdb
Source dataset
uspto-grants-1984_09
Patent number
US04472395

Reaction notes

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