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

HRID 2417791Notes

Reaction equation

HRID 2417791 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-hydroxybutan-3-one were added to the solution and 40 ml (0.5 mol) of pyridine were added dropwise to the mixture at 0° to 5° C. The reaction mixture was further stirred for 15 hours at room temperature and was discharged 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, the end product crystallising out. 46 g (71% of theory) of 2,2-dimethyl-1-tosyloxy-butan-3-one were obtained as colourless crystals of melting point 49°-52° C. ##STR11##

Workup

  1. additionwere added dropwise to the mixture at 0° to 5° C
  2. customthe organic phase was separated off
  3. washwashed with three times 200 ml of water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customthe end product crystallising out

Sources & evidence

ORD record
ord-bd558f319d7b43e5b21922e1e5bff5ca
Source dataset
uspto-grants-1984_09
Patent number
US04470994

Reaction notes

Loading…