Hydrochloric Acid → 2,2-Dimethyl-3-(toluene-4-sulfonyloxy)butyric acid methyl ester

HRID 2420733Notes

Reaction equation

HRID 2420733 reaction equation
[CH3:1][O:2][C:3](=[O:10])[C:4]([CH3:9])([CH3:8])[CH:5]([OH:7])[CH3:6].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.Cl>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:10])[C:4]([CH3:9])([CH3:8])[CH:5]([O:7][S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18])[CH3:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 10931571HCID 10931571, compound

Product 1

HCID 210314932,2-Dimethyl-3-(toluene-4-sulfonyloxy)butyric acid methyl esterYield 76%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled (0°) solution of 3-hydroxy-2,2-dimethyl-butyric acid methyl ester (52.0 g, 0.36 mol) in pyridine (100 ml) was added gradually, p-toluene sulfonyl chloride (69.0 g, 0.36 mol). The mixture was allowed to warm to room temperature and was stirred for 60 h. The reaction was again cooled in ice and was acidified by addition of HCl (2 M). The resultant solution was extracted with ethyl acetate, the extracts were washed with HCl, then brine, dried and evaporated to give an oil which formed a white precipitate upon standing. This mixture was dissolved in the minimum amount of ethyl acetate and then light petroleum was added to afford a white precipitate which was collected and washed with more light petroleum. The filtrate was partially evaporated and a second crop of crystals was collected and added to the first to afford 2,2-dimethyl-3-(toluene-4-sulfonyloxy)-butyric acid methyl ester (81.2 g, 76%).

Workup

  1. additionwas added gradually
  2. temperatureThe reaction was again cooled in ice
  3. extractionThe resultant solution was extracted with ethyl acetate
  4. washthe extracts were washed with HCl
  5. dry with materialbrine, dried
  6. customevaporated
  7. customto give an oil which
  8. customformed a white precipitate
  9. customto afford a white precipitate which
  10. customwas collected
  11. washwashed with more light petroleum
  12. customThe filtrate was partially evaporated
  13. customa second crop of crystals was collected
  14. additionadded to the first

Sources & evidence

ORD record
ord-221e94ac453f46baba243e62cce7cd00
Source dataset
uspto-grants-2011_06
Patent number
US07956058B2

Reaction notes

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