Hydrochloric Acid → Cyclobutylmethyl 4-methylbenzenesulfonate

HRID 27313

Reaction equation

HRID 27313 reaction equation
[CH2:1]1[CH2:4][CH:3]([CH2:5][OH:6])[CH2:2]1.[S:7](Cl)([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)(=[O:9])=[O:8].Cl>N1C=CC=CC=1>[C:13]1([CH3:14])[CH:15]=[CH:16][C:10]([S:7]([O:6][CH2:5][CH:3]2[CH2:4][CH2:1][CH2:2]2)(=[O:9])=[O:8])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 78130Cyclobutylcarbinol

Product 1

HCID 13163931Cyclobutylmethyl 4-methylbenzenesulfonateYield 105.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 24.4 g of Cyclobutane carbinol (prepared in Example 42A) in 570 ml of dry pyridine was stirred under argon at -10° C. and 81.0 g of tosyl chloride added in small portions. The reaction mixture was stirred at -10° C. to -0° C. for 4.5 hr, then poured into 1 liter of chilled 6 N HCl. The layers were separated and the aqueous layer extracted with ether-ethyl acetate. The combined extracts were washed with 10% aqueous sodium bicarbonate (NaHCO3), dried (MgSO4), filtered and evaporated in vacuo to yield 72.0 g of the title compound having the following physical characteristics:

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted with ether-ethyl acetate
  3. washThe combined extracts were washed with 10% aqueous sodium bicarbonate (NaHCO3)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8f19921b0ec84e5e914eba5e025e50e7
Source dataset
uspto-grants-1980_09
Patent number
US04220795

Linked notes

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